What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a lot of money in the process.
And on this show, I sit down with these IndieHackers to discuss the ideas, the opportunities, and
the strategies they're taking advantage of, so the rest of us can do the same.
I'm here with Matt Winsey, serial entrepreneur, and currently the founder of Summit.
Matt, welcome to the show.
Hey, thanks, Cortland.
Yeah, thanks for coming on.
I was reading through some of your tweets recently, and I saw this pattern of you sort
of holding, let's say, successful entrepreneurs to a standard of intellectual honesty, as
I think the way that you play.
And so there's this tweet you had about Justin—a tweet that Justin Kahn had, where he was like,
I'm going to tell you why storytelling is all about the only thing you need to start
a successful startup.
And you're like, for all your stories, you went to Yale.
You went to YC.
You exited a company for like a billion dollars.
Of course, investors gave you a lot of money.
That's not a story anybody could tell.
I mean, full credit for the first stepping stones of that journey.
Everybody comes, in theory, from very little.
But by the time you have the billion, maybe the $400 million you raised after that, maybe
you should discount that a little bit.
Just to throw a little bone to this few people here.
It's an interesting phenomenon, because even having a podcast and talking to lots of people,
I think, like when you're sitting in the chair and there's an audience listening, you're
trying to give advice, like you don't want to say, you know what, you can't do what
I did.
There's no way you can do what I did.
I had a special advantage, and that's what it boils down to.
Like, you want to be able to like share tips and things that people can actually follow.
But that might lead you to say things that like sort of ignore your unique advantages.
Yeah, we're all guilty of this.
I mean, I am as well.
Second time entrepreneur, I came into the second business with advantages.
I just want us to somehow acknowledge those.
And I realize you can't preface every tweet or statement with this whole preamble that
gets very, like it's irritating fast, you know, but, you know, if you're gonna, if,
I mean, honestly, though, it's like the bigger your platform, the higher your pulpit, like
the higher the standard, I feel like it's at least come back to that now and then, you
know.
Yeah, that makes a lot of sense.
And I think it's it's like a it's a tricky catch 22, because it's hard enough to like
write a tweet or a blog post or put out any content that like spreads and shares a message
to anybody like that in and of itself is hard.
Obviously, you get rewarded if you say more extreme things that are a little bit like
push the envelope or that like, you know, include really big numbers or say like, you
know, maybe even lie a little bit like those things are easier to spread.
And it's super hard to sort of like do both to like be extremely honest, but in all those
caveats that you're talking about, and also write something that influences a lot of people
and like affects people the way you want to.
I know.
And and the lesson that I have learned is that if you want to be effective in this world
in this business, it's like you said, you have to tell a story.
And I believe that people's attention spans like the amount that they're able to absorb
is very, very tight, very small.
And so I give you an example from my own world.
Like I I've done some fundraising for my second business.
I've had some good mentors.
They've looked at decks that I've created.
And there's always that team slide.
And when you when you pitch, you think that the team slide is actually supposed to be
your list of credentials or your history or what makes you so good at what you do.
And then you look at some successful team slides from certain people and it says like
three words.
And it's like PM at Facebook, you know, then I went to I see and then I got investment
from Sequoia.
There's like five words in their team slide and you're like, what's going on here?
It's like, oh, I see.
By team slide, you mean like who are the brands, what are the names that I relate to immediately?
And so like with my first company, there's this complicated version of the truth, which
is how my first business got acquired and merged into DHL, like the big global logistics
company.
But when I tell that story in a slide, like it really has to be distilled down to acquired
by DHL.
And it's like, that's not actually exactly right.
That's not true.
But like three letters is way more potent than a paragraph.
You know, that's that's the reality we're in.
So effective or completely thoroughly honest.
Like, I don't know.
It's tough.
It comes down a lot to human psychology, I think, which is the point that you're making
is it's hard to communicate something.
Even a simple idea, it's hard to get across.
And often if you relate something to something people already know, then instead of you having
to come forth and convince them of a million different things, having to tell a very detailed
story to let them know why you're impressive or why your advice matters, they can just
sort of like replace that with like, oh, Facebook trusted this guy, I trust him.
It cuts out a lot of the work that you have to do.
And suddenly, it's just super simple and it's like people describe their startups as like,
we are GitHub for XYZ, because then instead of having to give a whole spiel, you just
say like, this thing everybody already knows, but for X, it's the I like to say stories
are the original compression algorithm for trust, right?
For facts, it compresses all that down to I mean, a brand.
And it's now oh, Cortland's the extension of the Stripe brand.
Well, I love Stripe.
I trust Stripe.
So I trust Cortland.
Right.
And that's a very effective, potent, you know, five letter word or six, six letter word to
put on your resume compared to, I don't know, an essay on indie hackers podcasting.
Yeah, that's very true.
But when you think about it, it's kind of depressing because it's like, well, like,
it's not like it shouldn't be that convincing.
You know, you're just like, like, this shouldn't work.
But it does.
Yeah.
Yeah, it does.
So so here we are pragmatic and wanting to be honest at the same time.
Well, I think you are I mean, you mentioned you're a serial entrepreneur.
You've started two companies.
You've come a long way.
You've accrued some advantages.
Yeah.
Not to put you on the spot here, but what's something that you as an experienced founder
would want to, I guess, relate to beginning founders, something like that might typically
be a lot of bullshit out there that real founders aren't saying to beginning founders that they
should hear.
Oh, I mean, this this went across the airwaves recently.
There's the whole back and forth about, you know, is it about who you know?
Or is it about hustle and hard work and work ethic and all those things?
I think the answer is obviously both.
And I give you a story from my life.
I went to a great brand name school, University of Chicago, excellent in terms of academia.
And I went with a lot of really smart kids there.
I met a lot of kids there who actually made me feel stupid, which I think is the hallmark
of being in a good environment, you know, it's like, wow, I am no longer the smartest
person in the room that might have been the case in high school, definitely not the case
anymore.
And, you know, one mistake I made is I, after graduating college, I had friends that went
to Yahoo when Yahoo was cool, I had friends that went to Google after Yahoo when Yahoo
stopped being cool, I had other friends that applied to YC and, you know, all Silicon Valley
and maybe New York a little bit.
And so they kind of all went to those well-known places.
And I decided to go to a good, respectable company in Chicago.
They paid well, it was the right choice for my family.
And then I started my own business.
And looking back, I think, if you have the opportunity, I do think, just building right
off what we just said, if you can go work for a name brand for a few years and learn
those skills, your life is going to be easier because, like, I think I did that right when
it goes to where I went to college.
But then sort of after that, the entrepreneurial bug bit me so hard and I wanted to do that
so much that I just started my own thing and I went straight into, like, nobody knows who
I am or why they should trust me.
And that's like a hard place to start.
That's like starting, that's hard, that's hard mode, you know?
And if I had done what my friends did and I had gone to Yahoo for a few years and then
onto Asana, I think my life would have been really different.
Like, I think it would have been a lot easier to go raise that first round of funding or
whatever.
Why?
Because I'd be with other people who are like, oh, I've known Matt since, like, 2000.
You know, we went to college together.
Like, of course, I'm going to trust Matt with this angel money or whatever.
Instead, I really, I built my own business and I learned so much the hard way.
But then, like, communicating that to people was so difficult because I couldn't just say,
like, hey, I helped build the newsfeed.
No.
You know?
You got to write up, like, a thousand-word blog post so people have to read the whole
post if they want to know anything about you.
What's funny is I learned, like, all the same lessons, maybe even more.
But yeah, I kind of feel like I made a mistake.
Yeah.
And kind of the same boat.
I never worked at any sort of big company or any brand name company.
I went to a brand name school, which was great, but after that, I didn't get any real operating
experience.
You know, it was not PM at Facebook or anything.
And so I think I missed out on that.
I can't sit here and say, like, here's the lessons you learned.
Even right now, I technically work at a big company.
I can't tell you anything about it.
People email me and ask me questions about Stripe, like, I can't tell you.
Like, I'm doing any hackers.
I don't want to face it at all.
I'm, like, taking away zero lessons from this experience.
Let's talk about your first business, though.
It's called Stormpills, right?
Yeah.
Oh, that's right.
I did.
I'm one of the few people who did read your 5,000-word blog posts about bootstrapping,
Stormpills.
It's a pretty riveting story.
It's very detailed.
As I understand it, when you started it, you had kind of a humble ambitions.
Like, you didn't think it was going to be a business.
You didn't think you're going to make money from it.
And things just sort of, you know, one thing sort of led to another.
That's right.
I wanted to work on something.
Web 2.0 was a new thing.
Google Maps, just to put us in framing here.
Web 4.0, so Google Maps didn't have an API yet.
I wanted to work on a startup thing.
I was listening to podcasts that I would download onto my white iPod with a wheel on it.
And, like, listen to on the way to work.
And it had, you know, I don't even know if it had a Wi-Fi.
And so that was the world I was in.
But it was so exciting because I listened to this podcast by a fellow, and there weren't
that many podcasts at all, period, right?
So it was like this recording of a talk given by a fellow named Tom Coates, C-O-A-T-E-S.
And he talked about creating a data set that would just become the go-to place for some
domain, some kind of knowledge on the web.
Like this is the opportunity.
Be the destination for this kind of information on the web.
And back then, like, 2004, the web was small enough that, like, that kind of felt doable.
Like, I'm going to be the place where people go to for X.
And I picked weather because I had a bit of a background culturally with weather data
and information.
It was kind of a little, I don't know, geek passion of mine.
And really what happened was I went down this rabbit hole.
And the more I worked with the data, the more excited I got about the product and the technologies,
you know, started using Python.
A friend of mine introduced me to Python back in 04.
It just pulled me in.
You know, the creative abilities that I had doing that kind of work on nights and weekends
compared to what I was doing at my desk, even though I had a great job.
Like I already said, man, it was addictive.
And I had no idea how I was going to make money though.
That was the fact.
Yeah.
And your blog post you talk about every year basically the resources you were putting into
this company.
So it's like year one, you know, put in 300 hours and zero dollars.
Total revenue, zero dollars.
Year two.
100 additional hours, zero dollars in revenue.
Year three, a thousand additional hours, zero dollars in revenue.
It's crazy to think about how many actual years you're working on this thing and like
putting in like blood, sweat and tears and not making any money.
Like, do you think that what was pushing you to do this was just pure passion?
I think that's right.
It was the, it was that loop, that feedback loop that you get on as a creator where you
build a bit of code, you run it.
What comes back to you is like more valuable than what you put in.
You know, I suddenly realized, I was like, I'm creating value.
I don't know how to charge for it yet.
I don't even know what it's worth to anybody else, but like I love this.
And I like to say like one way to get way ahead of the market is to fall in love with
your product.
I mean, that that's good and bad, right?
By falling in love with it, you end up maybe way ahead of where anybody else in the world
needs this thing to be, but the more I worked on it, the farther it got ahead.
And I just realized, okay, this thing's powerful and I'm going to figure out how to charge
money for it at some point.
And then, and then I discovered SaaS eventually.
How do you, like, okay, let's say you're building a product and you feel like you love it.
You're like, I love this thing.
How do you tell, how do you differentiate between like, I actually authentically love
this because it's cool versus actually this is just my baby and I built it and no matter
how good or bad it is, I'm going to feel like I love it because I put so much time and effort
to do it.
Oh man, that's, that's good.
I mean, the litmus test has to be, I mean, it's obvious other people telling you that
I can say that I am a, I'm kind of addicted to, I mean, I'll say it this way because it
sounds the way it should.
I'm kind of addicted to praise.
I'm addicted to that validation, that external validation.
So when I create stuff, I don't keep it to myself, that's not natural for me.
So it's not necessarily that I'm proactive or disciplined about it, but when I make something,
I tend to share it and I share it and I share it.
So like the first thing I started to do, even when I was doing that was I was sharing what
I was working on with my manager at work, with my friends, you know, with my family.
And maybe I'm just also lucky that I have some like brutally honest friends and family.
I think that's really important.
Like I know the mom test is real.
So I didn't mention my mom in that, but if you tend to surround yourself with people
who can shoot straight with you, like, and you like to share what you're working on,
like that's a good recipe.
I think I had that.
And so I was able to show people what I was working on.
They're like, that's pretty interesting.
That's pretty cool.
And I also knew that what I was building was unique.
There wasn't anything else on the internet like this so that if I did succeed at it,
it would be the only thing of its kind.
And I'm like, you know, that seems pretty valuable even though I need to figure out
how to make money.
So what was it exactly?
This talk that you listened to was basically like you need to be a destination on the internet
for a particular thing.
You chose weather.
What specific aspect of weather?
Like why would anyone come to Stormpulse?
Yeah.
So in 04 as well, it was one of the most active hurricane seasons in history.
We had all these hurricanes that hit Florida, which is where I'm from.
And I was looking on the internet for information about these storms because my family was still
back in Florida.
I was living in Chicago, working in Chicago.
And I said, this is kind of crazy.
We have the internet, the web, which has these great tools.
But when it comes to weather information, which is this life or death stuff, you're
stuck going on these websites that are loaded with ads.
And there's a dude standing in front of a map waving his hands.
It's like a recording of a, it's like a recording of a TV like, um, spot that they're putting
in like this embedded.
I'm like, what?
It was just, it was so bad that I said, okay, I'm going to be this pure, clean, high fidelity,
get your facts on the weather.
Like five 38 people know that reference for weather or, you know, something that was more
grounded in facts and numbers and measurements and give me the data fast without the advertising.
That was what I was building and you know, that's a public service that's offered by
the government that that's their mission, but they got a lot of things to do.
And so it ends up being, it ends up being good in terms of the data quality, but then
it ends up being really poor in terms of the delivery, you know, so you're on weather.gov
and you're going, why is weather.gov the ugliest, like most old fashioned looking website on
the internet?
Like at the time.
And it's like, well, those, those people are scientists.
Like they're, they're trying to interpret the weather and figure stuff out.
They're not building Google maps or something like that.
So I said, what if I brought 2004 era technology to data that they've been harvesting since
the fifties, you know, like maybe we can pull this into the 21st century here.
Um, that was the idea with the caveat that of course the weather channel and these big,
big guys, they're doing that, but they've got a profit motive that is very much attached
to hype and page views and banner ads and all that stuff that is pretty harmful when
you're trying to use that information to make a life or death decision.
Like this is not just, Hey, this pop-ups in my way.
It's like, I want to see if like this tornado is heading to my, my house or place of business.
Like now is not the time for a pop-up.
Right.
Yeah.
So what does your, your, uh, your friends think?
You told me that you had some like critical friends.
People kept it real with you.
You show them this thing.
You're dumping out into it.
Sure.
On one hand, you don't have pop-up ads, but on the other hand, you're not making any
money.
Yeah.
Um, in the earliest days, I think only two people really gave me full credit.
One was my co-founder in that business, um, Brad, uh, and the other one was my, you know,
very, uh, faithful and supportive, uh, partner in life, um, sky.
And you know, those were really good balancing factors in my life where Brad's like, Hey,
I'm going to put in $40,000 in my own money.
That was his original investment.
He lent it to me so I could work on this product for a while.
And he was actually my manager at the first company.
So he's putting real skin in the game.
He's my first angel investor before I even knew what an angel investor was.
And he was kind of holding it out there and saying, keep building this amazing product
and we need to figure out then how to make money off of it.
Um, and then my wife was really, really fantastic because it was like, I finally built an amazing
product by 2006.
The product was pretty awesome.
But then it was like, okay, who's using it?
It's like, well, like 18 people used it today.
It's like, so you gave up the job as a software developer to work on a product that's being
used by 18 people and it's like, yeah.
So you know, those are good voices to wrestle with instead of just geeking out by myself.
It's such a good lesson there and that your co-founder was your manager because you have
this loop where you're going through, where you're naturally motivated to talk about what
you're building, which a lot of people aren't like, I'm not one of those people.
I'll build stuff in secret and quiet and no one will know about it for years.
Um, but if you're the opposite kind of way you are, people learn about it and then some
of those people might help you.
And they would never help you or join as your co-founder or fund your business or do any
of the good stuff.
If you weren't talking about it, what was the turning point with store, store posts
or were there multiple terms?
Cause I remember reading about like a widget that you, that you launched that was super
good.
Yeah.
Yup.
Yup.
There were multiple turning points.
I'll summarize the two.
One was we, uh, needed distribution badly.
And I just tweeted about distribution today.
This is funny because I'm a strong believer the product comes first, but then once you
have that, the 18 people doesn't get you where you need to be.
So, so you need that distribution and, um, we weren't making any money.
We also didn't have distribution.
We were languishing in obscurity, as some have said, I think it's a Paul Grammism and
I went and got a job at a newspaper called the Palm Beach post, which is the big Metro
newspaper in our area.
And I became a full-time developer in their newsroom.
What was neat about that very, very serendipitous was they had terrible weather data and information
and, and here I was working for them at this new day job because we didn't have it.
I didn't have any income anymore from the, from the start, or I burned through that whopping
$40,000.
Um, and I ended up figuring out how to, um, it wasn't that hard.
It wasn't like an enterprise sale, but it's like, Hey, would you be willing to embed our
weather maps into your website?
And that's what they did.
So we ended up going viral in terms of being embedded in other websites in 2008.
Um, and we started doubling traffic every day.
We ended up with millions of visitors.
We were on CNN USA today.
Um, it was pretty cool.
It's amazing.
The white house ended up using us, um, which is kind of a crazy footnote we, we, when I,
so I say we went viral is like, okay, I could wear a t-shirt with storm pulse on it at the
airport and somebody would be like, I love that site, which, which was, which is crazy.
And so very, very lucky.
The timing worked out.
My job worked out.
I was on the inside.
We got distribution, but we now were this weird fact of like, yeah, we have 4 million
visitors.
We're still not making.
Any money.
Really.
We did end up making about $120,000 that year.
I think 200,000 is the most we made, which allowed us to pay off some debts, credit
card debts, pay ourselves, you know, a very modest developer income each.
And yet we were still very far away from like making, making millions of dollars.
And, um, that was the next thing.
So the, so the next turning point was later, probably 2011, we were actually thinking of
shutting down the company, not shutting down the company, maybe selling it because we felt
like we had taken as far as we could.
And we also tried to raise venture capital, uh, at the time.
And you know, VCs were willing to listen because we had millions of visitors, but the business
model was so unknown and it was so hard for them to get their heads around like you're
going to charge money for a weather app.
Like that doesn't really make sense.
Like who does that?
Um, weather's free.
Like, so they didn't believe in the business model.
So we made this crazy decision to go from freemium and I would say poorly implemented
freemium to essentially paid only.
And we had, we still had a free plan, but it was like incredibly cripplingly basic.
And we made a lot of people really mad out of those millions of people that wanted the
product still, but we basically said, look, we, we don't have much of a choice here.
Of course they didn't know that we couldn't present weakness to the world and say, like,
doesn't understand like we're broke.
We don't have healthcare.
We have to do something.
So we just said, Hey, we're rolling out like a paid only plan.
And man, I had people calling me cause we had like a one 800 number that was like a
grasshopper number on the website.
It just went to my cell phone.
You know, they didn't know that.
So like, I'm taking my kids to swimming lessons.
We're not making any money.
And I have people chewing me out saying like, your management is so greedy.
It's these big cats, blah, blah, just like, and I'm like, I can't say like, uh, ma'am,
you know, like I'm actually like one of two people that works on this app that you've
been using for free for years and we just need to make money now.
So I'm sorry, but it was crazy.
We went from making a couple thousand dollars a month, uh, on our slow months and maybe
$10,000 in our busy months, 20,000 to, I remember we turned, we turned that paywall on and it
was April of 2000, I want to say 11.
I really pulled a lot of all nighters to get that paywall up because hurricane season starts
in June and we're like, we got to do this now.
So we did that and we made like 15 grand, I think in April, then 30, then 50, then 70.
And I think we made as a two person company, we made about half a million dollars that
first year where he said, we're going to charge for this thing.
And so, okay, now we're, now we're a real SAS business, you know, with thousands of
customers who are paying us and why did it take so long?
I don't know, but it was, it was brutal, man.
A lot of experience of people assuming you're much bigger than you really are.
I had a lot of that too, starting companies and like the 2000s and I think back then it
just wasn't, it just wasn't very popular to present yourself as like a face and a name
and to be very human and personal about like nowadays, almost everybody does that because
it's like there's nothing but advantages.
It inspires empathy in your customers and other people when they realize like you're
an actual person.
But when people will see you as this faceless corporation, it's almost like your hard work
works against you.
It's like your website's too polished and now everyone hates you, everyone thinks you're
an asshole.
Yeah.
It's like, I have a FedEx logo on my website because without permission, I put that logo
on there.
They think it's there because I've got like this enterprise sales team and I'm like making
millions of dollars and it was a catch 22 because we wanted large companies to trust
us.
Like we knew that a lot of our users that we wanted to charge money to, some of our first
customers were FedEx, US Steel, Humana Healthcare, like giant multi-billion dollar companies
where we couldn't say we were just two guys and a couple servers in AWS.
We had to present big.
But then those millions of users who really, really loved us, they just didn't know what
to think.
Like they thought we sold out completely and we sort of did, but we also had to.
It makes sense because you're trying to be two different things to different groups of
people and you had to kind of just decide, this is who we are.
This is who we're targeting.
We're going to keep this face of being this big corporation, but we're going to sell to
people who actually like that rather than people who don't.
Yup.
What do you think about, I think it's kind of fascinating that you had these huge customers.
I mean, like these aren't small names and you still were just like a two, three person
shop or something.
Do you think that comes down to that original video you watched that said be the destination
for something on the internet?
Like, do you think you really had something that was super unique that these companies
couldn't have gotten anywhere else?
I think so.
And it sounds very proud now, but if you consider that we spent five years working on this thing,
making almost no money, it's like, okay, if I spent 10,000 hours trying to be the destination
for X, you probably will become the destination for X.
And so we did have that.
I remember years and years later, let's say 2014, we got an inbound lead from Anheuser
Bush in St. Louis, like headquarters, and we're like, how'd you hear about us?
And they're like, well, somebody in one of our departments heard that we were looking
for a weather solution and they stood up, sort of purview, stood up in their cubicle
and said, hey, I used to use this site called stormpulse.com.
And it was like, it was where I went for everything.
Until they locked me out and made it paid only.
That's right.
But now with the corporate card, we have money.
We could probably sign up for the enterprise edition of that.
And so I think what we actually ended up benefiting from was the early version of like, bring
that product to work where weather is this consumer thing, everybody, everybody knows
somebody in their family that like is a weather geek usually, like there's probably somebody.
And then at work, people started having, you know, eventually, you know, we survived long
enough that eventually somebody's got like this weather problem and they're like, oh
yeah, I used to love that site.
Like I wonder if they're still around.
And that, that trust that they had in their personal life kind of got us in the door on
the enterprise side.
So again, clue me into this weather geekery phenomenon, because I actually don't have
any one of my family who said, what does it mean to be a weather geek?
What does that even look like?
This is so, this is, this is classic.
So I've also observed that like parts of the United States shard pretty sharply on this
dimension.
Like if you're east of the Mississippi and maybe like if you're east of Mississippi,
much more likely that you deal with weather in some kind of severe basis, like a whole
lot of people, sadly, a week this week, like we're killed in tornadoes in Kentucky.
Like and that affected thousands of people.
It's all over the airwaves.
A lot of other people didn't even know that happened.
And so a lot of our customers, yeah, you didn't hear a thing, but like it actually killed
more people than, than hurricanes and, and you know, a lot of other crazy events.
So they're digging through the rubble and it's, it's tragic.
And so I think I grew up in Florida, culturally Southeast United States, very weather exposed
and where the weather affected everything east, sort of the Mississippi, frankly, east
of the Colorado Rockies is where stuff just gets crazy.
And so we were sort of niche in that sense.
Like we, we got our roots and we got started with companies and people that kind of lived
weather year in and year out, day in and day out.
And so in these parts, maybe more so.
Now when we did go enterprise and we did go more international talking to folks in California
about earthquakes, wildfires, floods, tsunamis.
So we ended up broadening out into all kinds of natural disasters.
And we basically learned that, yeah, where you are in the world, you're attuned to different
things.
So if I talk to him about wildfires, you're like, Oh, okay, I know someone probably who's
dealt with that.
Yeah.
Yeah.
That's right.
Cool.
That makes a lot of sense.
I'm in wildfires and I'm in Seattle, so it's basically just like gray, gloomy, cloudy skies.
There's a few folks who've, who've insulated themselves from mother nature somehow.
And you're, you're like in this, you're in this cold, wet blanket.
People in San Diego are in this like cocoon of just dry 72 degree air for the rest of
the world.
Yeah, exactly.
Yeah.
So eventually what happened with Stormpost?
You sold it?
Yeah.
So we, we ended up selling it.
It was renamed at one point to Riskpulse because we broadened that beyond weather and we were,
we were acquired through a combination of private equity and DHL, who I mentioned earlier.
So DHL very interested in, well, logistics is their business.
We ended up going so far up market that Patrick McKenzie is well known for his charge more
mantra.
So he was an early investor in Stormpulse and we, he was one of the influencers on us raising
our prices.
So we went from four bucks a month to 40 bucks a month.
You know, our largest deals, by the time we sold the business, we're talking tens of thousands
of dollars per month to very large businesses to do what basically predict how the weather
is going to affect shipments.
So you think about, you know, 3PLs, logistics, supply chains, cargo containers and vessels,
mother nature wreaking havoc with all of that.
We ended up realizing that, wow, you know, people who are managing complex supply chains
around the world, they've got to keep track of this stuff because it affects their, affects
their business.
You know, that's what they do for a living.
So we were acquired through a combination of private equity and DHL to become a risk
analytics business that would track and monitor essentially all of these shipments all over
the world.
So that's what happened.
And I left in 2019.
That's so different than where you started.
I mean, it's the same, it's the same sort of well, right?
It's weather, but you started off like, I'm going to make the coolest 2004 version of
a weather site anyone's ever seen.
And then later on you're doing this like custom service for huge companies, helping them predict
the weather.
That's crazy.
It was, it was, and I really feel like it was multiple companies in a sense.
It was, you know, B2C originally, and then ultimately B2B enterprise SaaS where I'm traveling
around the country closing large deals and talking about things the way that a consultant
does.
Right.
And that was, that was where we ended up.
There's a talk I gave at MicroConf a few years back, and I like put all these colorful slides
on there.
One of the ideas I had was that like, you know, if you imagine that you're panning for
gold, you're digging for gold, not that anybody actually does this, you can dig like little
shallow holes, right?
You're going to go somewhere, dig a foot, you don't see any goals, move somewhere else,
or you could dig a really deep hole.
And the deeper you go, the more interesting things you uncover.
And I think it's very similar with like business ideas.
Like you stick in one particular area.
If you'd spent those 15 years hopping around and serve, let me try a little bit about the
weather.
Or that didn't work after six months.
Let me try something in games.
Oh, that didn't work after six months.
Let me try something in productivity software.
Like you probably wouldn't have found anything.
But because you went so deep into weather and deeper and deeper and deeper, you eventually
ended up with this cool niche where you're like providing this super expensive service
to customers that you never could have thought of from day one and nobody would have trusted
you.
Yeah.
I mean, to like put a fine point on the super niche part, you know, we were working with
Unilever to talk about at what temperature does Hellman's mayonnaise freeze and after
how long?
You know, so that they could ship it from Chicago to Los Angeles and you're like, wait,
there's money in that?
It's like, yeah.
And that's why that people call to talk about that you have to like a decade just obsessing
over these completely absurd things.
But you know, as they say, there's riches in the niches.
And so that was a valuable thing to be.
And then it turns out like is CPG small?
Like, no, actually CPG is is freaking huge.
It's just, you know, you don't realize that like to penetrate that market to be in that
market.
You have to be like the expert at this tiny piece of it.
Like I'm the guy that helps make sure that it's thermally protected when it's in transit.
You're like, that's a job.
It's like, yeah, like, do you know how much that stuff people sell every day?
Like, of course, that's a job.
Like there's a job just making sure it gets on the shelf.
So yeah, so I assume that you that that made you wealthy or made you pretty well off after
you had that exit.
But did you like being that guy?
Like when you when you set up shop to start your second business, are you thinking like,
I can't wait to be the mayonnaise freezing temperature guy again?
You know, I want to like, what are your goals going from business one to business two?
Yeah, after seven years, let's say, because we weren't enterprise at first, but I did
enterprise sales for basically from 2012, 2019, maybe 2014, 2019.
So after five years of enterprise sales, I was pretty burned out on enterprise sales.
And I did not want to do any more travel, raising a family, traveling to do sales pitches
and presentations.
Sure, meeting interesting people doing things I would never do otherwise, there were some
really awesome experiences from that.
But I realized that sales is one of those things that I was, I was good at.
I mean, was getting seven figure contracts done.
Now I was on team, so I could take all the credit, but like, I was leading deals that
were very, very large, and it was working.
And I learned to appreciate sales and be good at it because I had to but no, when I started
the second business, I said, I want to build a product business and see if I can keep it
a product business like, you know, looking at envy at people who are building tools that,
you know, are product led.
So that was my, that was my goal for the second business is to be product led and stick to
that somehow.
Why even start a second business?
I mean, if you are at a point in your life where like you got money, you've had a success
under your belt, you could do anything, you know, you can go write a book, take a break.
Why start?
Why being a startup founder again?
It's not easy.
I considered those things.
And I, yeah, why, why I think, I think I've been diagnosed by my family as being, as you
said, a serial entrepreneur, and I don't think I don't, I don't want to brand myself in a
bad way.
If I were an employee, again, I would have to be in a very entrepreneurial role within
that company.
So yes, those exist every once in a while, some series A or series B or whatever founder
will find me on the internet and say, Hey, Matt, like I'm looking for an entrepreneurial
kind of person to lead this or do that.
And so I considered maybe now I should do what I didn't do in the first place and go
join some fast scaling startup.
I don't have to be the guy that carries the load or the gal that carries the load anymore.
Wouldn't that be nice?
You know, I don't have to fundraise and do this stuff.
Just I've got stock, I'm killing it, contributing, got, you know, this, like I considered a few
of those roles and it was so tempting, but, but like I had another idea and I just started
testing that idea, validating that idea and I'm like, Oh great, you know, here we go again.
Like I feel like this idea, it's time is now and I'm the guy to work on it.
So okay, here, here we go.
Here we go.
I, I, here we go.
And I did do a couple of things like I, I decided I was not going to spend my personal
savings on this second business.
Like it was not fair to my family or me to like take the winnings in the last business
and immediately plowed them into the new thing and say like, let's double or nothing.
Like no, I'm not doing double or nothing.
We are doing, let's try this out.
You know, we're going to sell equity to bankroll it and I'm going to sacrifice some income
because I'm not going to pay myself well for a while, but I'm not going to go double or
nothing and be the like primary investor in this business.
Also having experience with SaaS, knowing that sure you go double or nothing thinking
that you just need to give yourself X. You actually need two X, three X, four X and now
you're way, way over.
And I didn't want that.
I wanted to do something that was less stress and kind of fun, you know, a less stressed
approach financially.
It makes a lot of sense. I mean, you have a tweet here about things you're not doing
at your second startup and a lot of the things you're not doing are like super stressful
things like you're not hiring fast, you're not chasing higher evaluations, you're not
doing enterprise sales hunting for whales, not having co-founders.
That's an interesting one because one might argue that having co-founders makes your job
easier.
It makes you accountable to somebody, yes, but it also sort of spreads the load, shares
a burden across multiple shoulders.
I think it does at first and then I think if it takes twice as long or three times as
long as you think, now your carrot is just so much smaller, you know, and then the stress
is different.
It's not like the amount of work you had to do.
It's the reward that I get for this work is now half as much, a third as much.
I was actually more worried about that stress because of how long the first company took.
The carrot is too small now, stress, versus if I find Heroku and I learned some of this
and some of that, maybe I don't need a CTO.
That was the idea is that I could use tools to carry the load and building the shoulders
of giants and then keep the carrot big.
That was the goal.
Makes a lot of sense.
I also follow a similar path of doing things on my own, although I brought on my brother
as sort of a late co-founder, which has been great, but I think another sort of underrated
or underappreciated aspect is that when things are going well, it's very easy to get along
with the co-founders.
If things are going poorly, it's very easy to look for blame or to try to figure things
out.
I think that commonly creates sort of strife and disagreement between co-founders is going
to be very difficult.
Not only is your shape quite smaller because it's dragging on, but you're also potentially
fighting with somebody else and that's not great.
I want to asterisk cross next to that, have partners, have co-workers, have teammates,
have advisors.
If you're good at assimilating and integrating constructive feedback from people, hire people,
but don't mistake your first hires for a co-founder because those aren't the same thing.
That's a lesson I learned.
Another couple of things you put on your list, you're not accepting speculative meetings.
You're valuing.
This one's sort of tricky because you have two or you're sort of valuing things in certain
orders.
You're not valuing talent over values, nor are you valuing potential over talent.
I bet you're basically saying values come first and then talent and then potential.
Yeah, I think so.
I'm flexible.
I don't want this to be religion.
Part of that is the stage that I'm at.
I'm very early stage.
We have three and a half, I like to say round up of four people now at this company.
Potential is awesome if you have the resources to nurture people and grow people and yield
the fruits of that potential.
If you're this early, you need people who are going to contribute immediately, not need
a lot of development, and you're doing them a disservice to bring them on as a junior
person when you need a senior level skill set.
For now at least, not that, and then the values over talent, I think that's pretty straightforward.
I've hired mercenaries before, just do so very carefully.
It's like the Phil Jackson quote.
You can have a Dennis Rodman, but you can only have one.
If you need rebounds, do what you got to do, but if you start filling your company with
those, it's not going to work out.
You got to be very, very careful to bending these rules.
I think my favorite thing on this list that you have is your rewarding results over process,
which I think I've talked about on the show before, but it's a big part of how I've changed
my life in the last few years, which is to care much more about what I'm doing day-to-day
and how I'm doing things rather than whether or not I hit some particular goal or got some
pot of gold at the end of the rainbow.
I think sales cultures, historically or traditionally, maybe stereotypically are results over process.
I think that's where a lot of them fall, the mediocre ones.
I mean, Risk Pulse went through those phases, Storm Pulse, where it's like, did we get this
deal closed?
Did we move it through the pipeline, et cetera?
It doesn't scale very well.
The problem is you end up with this situation where you have a bunch of heroes who are delivering
results, whatever it takes, however it takes, like burning the midnight oil, whatever.
It's this hero culture, whereas I think process culture is, hey man, I did my part, I contributed,
I moved the thing from here to there.
In the end, we didn't get the result we wanted, but we called the play, I ran my route, I
didn't catch the ball, but we should call the same play the next time.
It doesn't mean that we called the wrong play.
What's nice is you shed a lot of blame then as well, because as managers, you're building
a company.
If you just blame individuals for not delivering results, you're missing process improvements.
I think this is not the dream, but think about when the process gets good enough, the people
you can hire, you can start to bend that other rule of like, hey, we can hire somebody who's
more junior, put them in this role with a really, really well-defined process, and they're
still going to be able to deliver the results we want most of the time.
That's a scalable company.
It's a mindset shift for sure, and it still comes up to this day like we botched a, a deployment
was botched in the last couple months, and I looked at the process and I'm like, this
is my fault.
I'm the one who decided that we were going to do this late in the day.
I'm the one who decided that we were going to do it without the clear communication
we need.
Like the process was just bad, and I can sit here and blame the person who shipped a bug,
but like the process is bad.
So like, even if we, even if we truck that out and do that ceremony where we blame the
person for doing this, like we haven't gotten better, you know, um, literally we're just
going to probably have the same mistake rate going forward.
So we haven't made progress.
Yeah.
I think you need to be sort of focused on the process itself if you want to lock in
those wins and make it so you can continually make those wins.
And for me personally, I think the best thing about process over goals is more just like
the sort of mental health happiness part of it, because if you have a startup, like you're
going to like, sometimes like things are going to go poorly.
Like just, it's just going to happen.
But if you've set up the process, like your day to day working style or your, your systems
such that like you can actually enjoy them and the process is kind of the point, then
like you can still be happy even when you're not hitting your goals.
I think that's pretty crucial because like the happiness at the end of the rainbow, like
it doesn't last that long, right?
Like you sold storm poles.
You're probably not doing a little dance every day when you woke up, when you wake up about
selling storm poles.
It's a couple of years ago, you're already over it, you know, but the process of like
running that business was 15 years.
The process of running summit right now is going to be years.
Yeah, that's right.
And I think we could learn a lot more from sports than we let on.
Like what do those people do?
They're process monsters.
You know, it's like you miss all these shots, you miss all these, you know, all these strikeouts,
all these things.
Those people that's like, I'm going to swing the same way, you know, a hundred times and
I'm still going to be like maybe MVP of the world series because I just stick to the process.
Like that's incredible.
But anyway, there's a whole cultural thing.
I think there's, there's so much to learn from that.
And I'm trying to get better at that this time around for sure.
Well, starters and scarier, you know, you don't get a hundred, you don't get a hundred
at bats.
It's a startup powder.
You know, you get like a handful in your life and yeah, yeah, that's, that's fair.
That's fair.
Um, but you know, as, as Eric Reese and Steve Blank and a bunch of other people have shown
us like, boy, there's a whole lot more we could be doing on the process side.
So yeah, a lot more.
Yeah.
So, so tell me about like a summit here.
You come up with this idea.
You're like, the world needs this, uh, what was the idea and how did you get started with
it?
Yeah.
So I was building that last company and somewhere around 2014, we started getting those big
enterprise contracts.
We needed money.
We needed some venture capital to, uh, hire salespeople to go after those big deals.
And we knew that, man, these deals take three to three months, four months to close.
That means we need to figure out really like how much money do we need to scale this business
that we think we figured out.
And I remember building, uh, I wasn't building financial models.
I remember looking at financial models that were being built by others in the team.
And then I would be in these investor meetings and I'd pitch and say like, yeah, we need
this money to go after this market, this enterprise market, these anhyzer bushes of the world.
And I want to hire an enterprise salespeople.
We know that, you know, those people take time to pay off.
They're like, great.
That sounds good.
One question like if the sales cycles go from 90 days to like six months, let's just say,
how would that change the amount of money you need?
I was like, you know, that's a great question.
Let me get back to you and let you know.
And I remember going back to the team that built these models and they told me like we,
there's no like cell in the spreadsheet where we can just change it from like 90 days to
180 days.
And then everything just updates automatically.
Like every column has to be shifted.
Everything has to be thought through.
We have to basically rebuild this entire model to anchor off of a different assumption from
a sales cycles length standpoint.
I was like, what?
That's not how software works.
Like software where like you just changed one thing and like everything just automatically
updates.
Like, yeah, but this is, this is a success sheet that we built.
Like that's not how it works.
Like, wow.
So I had that I thought in 2014, I remember just for fun building some Python scripts
that did play around with these kinds of things.
And I shelved that idea in 2014, 2015 and said, Hey, if I ever work in another thing,
that's going to be one of the ideas that I consider is like, that's insane that you can't
just quickly answer that question.
And then 2019 comes along and I'm looking for the next thing to work on.
And I asked a couple of friends of mine.
So Nick and Steli over at close.com.
I was like, okay, you guys know sales cycles lengths really well.
You guys know sales.
You guys know startups.
I were to tell you that I wanted to model like how this would change things.
Is there a, is there a product for that?
Like, no, no, we've never seen anything like that.
Like there's no, there's no Carta for financial models where you can just manage this thing
outside of a spreadsheet.
It's like, what?
It's like, okay, this is exciting.
This is, this could still be a thing.
And like, good thing I didn't start on in 2014 because I would have spent like five
years still waiting for anybody else to care about this idea.
Right.
Why do you think now is the time, like what made, what made 2019 different than 2014 in
terms of people caring about modeling this stuff?
So it became a couple of things happen.
One is financial data started to move into APIs, you know, the cloud as the, as the consultants
say, where you can just go get your Stripe data.
You can go get your bank account information through Plaid, um, Kodat now has accounting
data that you can just download and suck up.
And so I had this idea of like, okay, the date is now available.
It's not locked in some file on a desktop.
Um, and you know, interfaces are getting powerful enough.
Like G sheets is mature.
There should be a way to do this in a more, um, web centric fashion.
Then I looked at something like Figma and I'm like, wow, Figma is like a great example
where you're now moving a desktop app level, you know, interface and processing power into
the, into the browser.
So we should be able to build something that does this in the browser.
Now let's give it a shot.
And I spent probably three or six months sort of validating the idea with some prototypes
and ideas and wireframes that I bounced around some founders that I had met mostly at the
business software conference, which is a great conference.
So I met folks there, shared the idea with them, said, Hey, is this a problem that you
deal with?
They all sit, you know, a lot of them said yes.
And kind of like the last time that I started just working on a product that I was going
to love, like, can I build something that I love?
How do you, validation process is so tricky because I think there's a pool in both directions.
Number one, there's a pool of like, Oh my God, I'm so excited about this idea.
I want to just start building it.
And if you weren't excited about it, you wouldn't put in all this work to validate it.
So you already have that excitement from day one.
But then on the other hand, there's like, Oh, I should validate this idea.
And I should go through the entire sort of correct process of validating issues.
The mom tests, it asks people what they're already using, I should do surveys and all
sorts of stuff.
So I don't waste time.
We can be doing that for literally years.
And so how did you decide that like, okay, six months is the right amount of time before
I dive into this headfirst?
Yeah, I, I did a lot of socializing of the idea, floated it sort of just started collecting
thoughts from people of like, Oh yeah, that's a problem.
But actually this kind of put that all to a big, you know, sort of mental cauldron,
if you will, kept stirring, kept stirring.
And then I'm a builder.
So I didn't build like the version of my dreams.
I, I didn't build mockups though, really, I built, I did build workable prototypes,
but I didn't care at all about what it looked like, how crappy it was from a UI standpoint.
Like I did the first version was like bootstrap for the UI, you know, charts, JS for the charts.
I didn't care about any of that.
All I cared about was like, Hey, if I gave you a thing where you could put in some numbers
and hit a button, is that cool?
Is that useful?
And like, you know, Nick and a few others said, Ooh, this is cool.
This is cool.
I'd like this.
And that just started me on the loop of like, okay, what do you like about it?
Why?
And I would basically pursue that until I hit a wall and I hit a wall a few times and
I had to kind of backtrack to get to where we are today.
But I'm big fan of, especially in such a big market, I think one lesson I learned was like
try to do a breadth first search, meaning like, just test this, test this, test this,
go in a full circle.
It's just like spiraling, spiraling, spiraling where, you know, you test and then circle
test and then circle.
I think I did that for six months, mostly because by the time I got six months into
it, I knew I could charge something for this version that I have.
And I started to do that.
And then I started to just get some pull from the market, like people going, okay, this
is fun.
I like this.
I've never called a financial app fun before.
So you know, this is cool and I'd probably pay 50 bucks a month if you added, you know,
a QuickBooks integration or something.
So it just, yeah, it just started to snowball.
And I also wrote a bunch of essays on Medium that were financially related, kind of financial
modeling centric, just to try to see if I could become known as somebody who knew this
space well and get feedback just from people who maybe just asked me questions about financials
because I wasn't a, I'm not a CFO.
I'm not a FinTech guy by trade.
Like that was my background.
I was a CEO and I dealt with financials, but I kind of had to steep myself in this new
role of, okay, I need to know the financial market really, really well, which included
experimenting with things like Stripe and Plaid and everything else to become an expert.
So you mentioned hitting like a lot of these walls, these blocks and then having to sort
of back up and figure out what to do next.
I think probably safe to say that's like most founders experience that they hit some sort
of wall.
Like most businesses don't work out, at least in my experience.
But what most people also don't do is like learn how to back up and then take another
path.
And that's something that you've done at least a couple of times with Summit.
So walk me through like what does it look like to realize that what you're doing is
not working and then successfully figure out a different path for.
Yeah, maybe two ways to split this.
Like one is, is the product, is the technology working?
Like there's, there's that part of how much technical debt can you absorb?
Can I add this next feature without going bankrupt sort of technology from a technology
standpoint?
Those, a lot of listeners probably know when they're getting there.
And I think a little bit technical debt is perfectly fine because the goal is not to
build something without that to start.
Like that's premature optimization.
I got there a few times, had to refactor, but where I really hit a wall is you don't
want to, the walls that I'm talking about, they're good walls.
They're the kind when you say, wow, okay, the market, the customer, the prospect is
asking me to do one more thing.
And I want to be able to serve them that I want to do that because like, this is the
customer I want to serve.
This is the use case I want to tackle, but the current product can't do that.
Like it's not, why it's not designed for that.
And I think the real question is knowing, okay, it wasn't designed for that because
I didn't expect this to be where I would end up like, okay, it's really popular.
I wasn't expecting it up here when I designed it in the first place.
You know, you're asking me for things that I did not incorporate into my initial design.
That is a definitely fork in the road.
And I'm not saying it's always right to go back to the drawing board, but you can develop
your sort of Spidey sense about, okay, what am I hearing and is it in common enough?
And going back to the drawing board is like a really, it's a bigger bet, right?
So maybe, okay, I can satisfy this need manually.
I can write the report.
I can do this thing.
I can do that thing.
And I don't have to go back to drawing board.
I can just add incrementally more efforts or features to this product and satisfy that
demand.
But if you hear enough of that and that's common across all of these customers, then
do you really want to build a business on top of like duct tape and band-aids?
Like what you're basically, what, congratulations, right?
You've sort of learned what you should have known in the first place.
And now that you know that let go of what you built.
If you can, if you can afford to, I know it's a luxury, but I usually do this after fundraises.
I would raise money based off the traction and progress, which I've done a couple times
for Summit.
And then right after raising money, I would sort of take stock, stop and say, is this
the foundation for the next phase?
Because I just learned a bunch of stuff.
We've got some traction.
If I keep going forward, this is the foundation.
I'm baking that in.
I'm locking that in.
If I burn it down now, if I tear it down now, I can rebuild it as if I knew that in the
first place.
And now my foundation is clean.
It's ready for more learning.
Every time you learn something, you kind of pollute or you have to adjust your plans.
And I feel like one way to reward yourself, say, if I get traction, if I get this far,
the market responds.
Knowing when to resist the temptation to keep going and instead say, okay, stop.
We the market's responding in a way we didn't expect.
We built the Band-Aid version, the one-off version.
Let's rebuild that now because that's actually the new foundation we want to build on.
And again, that's a luxury.
There's no easy answer because if you don't have the time to stop and rebuild, you don't.
There's no way around it.
But I was lucky enough with Summit to have those opportunities.
So it's sort of, sorry, investors, I know you invested in this one thing last week.
Now that I have all the money I need to feel safe and secure, I'm doing a completely different
thing.
And starting to scratch.
Yeah.
Yeah.
I mean, I may not be proven honest.
I've done that three times now.
Three times.
How do your investors feel about it when you tell them?
Super supportive, frankly, because they're early stage investors.
They're like, we bet on you, Matt.
We believe in you.
And if what you're telling me is that the current product isn't going to get us to where
we want to go, like, you know, this better than we do.
We trust you, you know, and I just to characterize, like the first version, I couldn't add features
fast enough.
It was, it needed to be rebuilt.
So I did.
The second version was a little bit trickier to diagnose because it was working.
I was making money, people were signing up, but they were also canceling.
And then my best customers were asking me to essentially perform services for that.
Like I would tell my wife, like, Hey, I got to work tonight.
Like this, this customer of our of mine, like needs this report, which isn't a feature yet.
So I'm going to like sit there, hack on the database a little bit, generate this data,
send it to them via email and like, what is, what is going on here?
Like, what are they really asking for?
And in theory, we could have built a decent SAS on top of that model, but it would have
required scaling headcounts significantly to deliver those services, enterprise deals
to justify that time that was being invested.
Right.
And it would take me down the path that we talked about earlier.
Like that's not the kind of business I wanted to write.
Right.
So it's like, sorry, I can't, I cannot build this.
I'm not the guy for this.
So what can I build instead?
Yeah, that's, I mean, it's scary because it's a huge decision to have to make, right?
Like, okay, you see a path to make money.
Maybe there's reasons not to go down that path.
Maybe it's hard.
Maybe it's sloppy.
Maybe you're good.
Business is gonna look like Frankenstein.
You're gonna end up doing things you don't like, but it's like, people are paying you
money for this.
You know?
Like, yeah.
And the other path is like, well, you kind of look your finger and stick it in the air
and like see which way the wind is blowing and like, oh, just go do this different thing.
Like, do you need, like, do you need like hard data?
Cause I know like, I think the biggest change you're talking about is moving from like summit
version two to summit version three.
And I saw this graph that you tweeted about it where you were like, we burned the boats.
And so for like two months on this graph, like the number of customers and subscribers
you have was going down after going up consistently for years, it was going down because you made
this change.
And then after that, it started skyrocketing and growing at a pace that hadn't grown beforehand.
And so you had a lot of conviction to make this huge change to your product, but like
it had to be scary saying like, screw what we were doing, screw our earlier customers
and what they wanted.
Like, we're not doing this anymore.
And like, I don't, I guess what I'm trying to figure out is like, how do you have the
conviction to do that?
Like, what made you so certain that the path you picked was the best one, even though it
wasn't directly what people are necessarily asking you to do.
We had 12 months of history.
And I would say with the product that we were about to burn down, it wasn't quite 12 months.
It was more like six months, seven months with the product before we made that decision
and then another five months of building the new thing.
So by the time we canceled all those subscriptions and essentially gently fired those customers,
we had been in market with it for a year.
If you know what you're looking for, if you know what success looks like, like success
to me was steady growth, three, four, five, six months of growth and modest churn.
We weren't seeing that in the numbers and at some point you're like, okay, it happened
once.
Well, let me change, like make a little change.
Like second time, oh, we had a month of growth, two months of growth and then we shrink again.
It's like, okay, like let me change another thing.
But like the third time it happens where, okay, this product, this business doesn't
deliver the kind of growth that you've defined as success.
It's like, okay, we took the car around the track.
It didn't perform.
We tweaked some things, took her out again, tweaked some things, took her out again.
It's like, you know, use your analogy, like by the time something that you built doesn't
deliver the outcome or results you want, how many times do you need to do that before you
go, okay, this thing, we need to scrap everything but the chassis, right?
Like something, like we're going to keep whatever we like and whatever's working, but we can't
get there from here.
Like there's, this is never going to perform the way we want it to.
Like, but we believe we know what we want it to.
And one thing that we experience, and I feel like a lot more companies or startups should
consider this.
We were getting all of our best customers in that previous version of the product.
They were all asking us for different things, for, for flexibility, essentially.
They're all asking us for different things.
So I wish I could do this.
I wish I could do that.
And the common thread was, okay, whatever this new thing is that we build, we have to just
go all in on flexibility.
Like it needs to be the most flexible thing that we've ever built.
Way more flexible than the last versions by a whole level of abstraction.
And so now we went back into this design room with just the chassis, four wheels, and like
this thing needs to do X.
And that's so, that's such a relief when you're like, okay, we now know that the market wants
flexibility.
What's the most flexible thing we can possibly deliver in six months?
That's the, that's where the confidence comes from.
And then the other part is going, you know what?
If this fails, this is the game we're playing.
Like we're in this thing to get a big outcome for me, for our investors, for our stakeholders.
We're not interested in a small lifestyle business, if you will.
That's a loaded word, but knowing that success looks like this, that we're not achieving
success and then going into design, the design room with 12 months of consistent feedback.
It's almost not a hard, it's not even a scary decision at that point.
That makes sense.
I think like the thing that I'm hearing is that like you had a very concrete sort of
objectives in mind where you could say like, we are on track or we are not on track.
And I think with a lot of founders, it's kind of like, if you don't know where you're going
or where you want to go, it can be hard to make these decisions.
It's like, well, we're making some money and should I cut ties with this and move on?
But if you're like, no, we're trying to be a huge company and it doesn't matter if we
have a little bit of traction, that's not going to get us where we need to go.
So it makes it much easier to be like, this current trajectory is a failure, sucks to
give up what we have, sucks to give up the customers that we have, but we can do that
and rest easy because we know it's objectively not working.
And you have to have some sort of like North Star to know that.
Absolutely.
And yeah, we knew we couldn't get there going down the path we were.
The growth path down the path we're going was going to be very difficult.
And it was going to be a very different kind of business than we wanted to build.
So it failed for all those reasons, but we had learned so much and it was good for that.
It learned a lot.
So we doubled down, we hired a full-time front end developer on contract basis, rebuilt the
entire front end.
I rebuilt kind of the middle layers, if you will, the engine, and we took it to market
in July and it's what we hoped for.
It has a good ending.
Yeah.
I'm looking at your graph and the graph of your subscribers is the first, I don't know,
eight or nine months.
It was kind of flat, pretty low, and the next 12 months it was like a plateau.
It was like you kind of shot up, but then kind of stayed kind of level-ish for a while.
And then you see V3 and it's like a mountain just shooting up into the sky.
It's like, okay, that's great.
That's completely different.
And I've been stuck in this trap where it's like you keep doing things and you plateau.
You go up a little bit, but then you stay straight, you're not sort of unlocking consistent
growth.
Specifically, what was it that you changed?
I mean, you just added flexibility and then people started recommending the product to
each other.
It sort of turning less.
What enabled you to grow so much more after this change?
So we realized that we had been trying to, the first version was we're going to create
a financial model that everyone's going to use.
And you put in your numbers and you click the button and here's the answers.
The least flexible thing.
Yeah, the least flexible thing.
I called it like a vending machine for a financial model and it only serves one kind.
It's like everybody puts in the same coins and gets the same thing.
Maybe you have like five choices.
But the second version was like, okay, you want more flexibility?
And I was talking to Corey Haines, great example.
He was at Bear Metrics at the time and he's like, Matt, I've got multiple marketing channels.
Your model only has one.
I want another.
So the second version, we're like, cool, Corey, like now you can add a second marketing channel.
So it's like, it was a very specific complaint.
Yeah.
So it's very specific complaints like, okay, we had the first version and the like V one
and a half where he could add his extra thing in there.
V two was like, okay, nevermind.
It's like, you know what?
People might have one or more of all of these things.
Let's like, let them basically configure the heck out of this thing.
But we were still constraining them and saying like, but you can only use the building blocks
that are on the table.
Like there's, there's 40 building blocks and you can configure them however you want.
So suddenly like the number of financial models that people could build was, was multiplicatively
more.
It was like thousands more, maybe tens of thousands more.
But then people would still come to us and go, Hey, this is cool, but I run an e-commerce
business and I've got cogs attached to every sale and actually those costs are going down.
So is there any way to model that and we're like, what is going on?
Like we're either going to have to build like super bloatware.
It's going to end up looking like, you know, some Microsoft product with like 50 drop downs
and buttons.
And like, you know, how can we possibly please the person who wants like 25 fields on their
model and the person who's like, I just have, I just have one number, you know?
And so the only thing more flexible than, so we start with a form and then we went to
a form of forms.
That was the second version.
The third version was like, what's more flexible than a form of forms?
It's like, well, a language would be more flexible than a form of forms because a language,
if you think about it as kind of the ability for me and you on the fly, just create these
structures out of nothing.
Like you can have a sentence that's really long and run on and has seven commas in it.
Or you could be like Ernest Hemingway.
If I want to sit down and talk to somebody about their financial modeling, they can just
describe it to me using the English language.
Exactly.
Exactly.
And just let them.
But it's software, it's hard.
In software, it's very hard.
And if it turns out that every single time somebody says, but I also have this, like
there's another feature you have to build your DOA man, like you're never going to satisfy
the demand.
And that's what we realized excels the incumbent in this space.
The reason it works is they, it's infinitely flexible.
It's a language, but it's even worse.
It's actually not one language.
It's more like a set of languages and everybody has their own dialect.
Like you ever come into somebody spreadsheet, like they are speaking their own language,
even though it looks the same.
Use the same alphabet, but like it's not the same language.
We realize that, wow, if we don't get people flexibility, this market, and I think this
is hopefully take away for others.
Some markets there's this inelasticity.
What I mean is let's say you build three features.
If you build three features for a financial model, you get like one credit.
Okay.
If you build 30 features, you get two credits.
If you build a thousand features, you get like 90 credits.
Okay.
So what we realized was like, wow, okay, we want a ton of credit for this thing.
We want to capture as much value as possible.
But the burden that we're like the mountain of features we're going to have to build is
infinite.
Crazy.
Crazy.
It's impossible.
So the only way to possibly scale this mountain is to give people a language and we're going
to strategic trade off here.
Hey, Cortland.
Good news.
You have all the flexibility you could possibly ever want.
The only catch is you have to learn a slightly new language to express those ideas, right?
You're like, okay.
Like I'm, I might be willing to try that because you're basically saying that you're no longer
going to restrict my expression.
I can express anything I want to.
But the trade off is I got to learn something new, which that's not fun, but could you make
it fun?
And so that's what we did.
We released a canvas with a language, super flexible.
And now we hardly get any feature requests.
Like we get feature requests, but they're not the kind we used to get.
It's never like, Hey, can you add this feature?
It's like, can you make it faster?
Can you make it, can I, like, is there an API?
Like they want like the whole product to expand, but the core product, they have like really
nothing to say other than, Hey, I want to keep learning it.
Like I want to get more fluent in it.
So it's like your product can solve their problem and they just want you to solve it
better, faster, cooler, but they're not like, Hey, this doesn't solve, this doesn't let
me solve my problem.
Like it does.
That's right.
Yeah.
You make it faster.
And I'm like, that's fantastic because there's no diminishing returns on speed, right?
We can just keep making it faster.
And all those complaints about the inflexibility went away and people are adopting it and they're
leaving spreadsheets for this kind of exercise because we're 95% flexible.
You'll never be as flexible as like an Excel sheet where it's like, you can do anything
as much as you want.
Like we can't do that and still be good software for what we're trying to do, but we were able
to overcome that flexibility objection and now we have the subscriptions to prove it.
That's crazy.
It's pretty rare that I have someone on the podcast where I talk to them and like the
actual problem that they're facing is their product just wasn't the right product or wasn't
good enough.
You know, people pivot a lot and then, but it's like usually like a distribution.
I wasn't selling.
I wasn't talking to customers, et cetera, et cetera.
But it's cool to hear that.
Like, no, no, no.
Again, you dug this really deep hole.
You went really deep and to financial modeling and talking to your customers and you learned
a lot of lessons that you could not have learned if you hadn't actually started building and
selling the thing and had customers using it.
And then you came back out of that with like this unique insight and unlike the storm
pollster, it was kind of like, let's pick a crazy niche.
It was almost kind of like the opposite.
It was like for this particular segment, we need to go super broad and flexible, otherwise
it's not going to work because everyone has their own idiosyncrasies.
That's right.
Yeah.
So that lesson was carried over, but we went completely horizontal and flexible.
And what we've also learned in the process is that we're not really just about financial
models anymore.
So we've really developed a language that people can use to build models.
And when I talk to companies, they've got onboarding models, they've got sales models,
marketing models, pipelines and offboarding, all these, you know, my AWS spend model.
Like models are kind of everywhere.
And we had this blinder vision of the CFO suite, you know, the financial model, like
the P and L that, you know, the, the Tabula Rasa, that the thing we're like, wait a minute.
No, like actually, Cortland makes most of his decisions with models that he builds either
in a notebook or in like a really tiny little G sheet that he might be embarrassed to share
with, with me if I asked him to look at it.
Cause you're like, ah, this isn't, this isn't like professional, whatever.
So we ended up reaching a whole new audience.
Okay.
So I've got so many more questions I want to ask you, but it's already going long.
So I'm going to try something I almost never do on the show, which is like a rapid fire
section.
Okay.
The challenge is these aren't actually rapid fire questions.
They're not intended to be answered rapidly.
So I will attempt, uh, okay.
First thing, uh, and researching summit, your homepage is like crazy simple and your website's
basically just one page.
Uh, why is that?
Why is it not more extensive?
I want to dive into the product and learn more about it.
Why keep it so simple?
Because the risk to our business was will people keep using the product?
Not can we get people to sign up for the product.
So we really have focused on testing usage and engagement as opposed to the homepage.
We're willing to lose homepage visitors for now, knowing that we can just get the people
that try it to stay.
Then we can invest in the homepage with confidence.
It makes sense.
There's like this funnel of acquisition, getting people to your website, converting them to
customers and then retaining them.
And if you don't have the retention part at the end, then the other parts don't matter
because you got a leaky bucket.
That's right.
Makes perfect sense.
Uh, number two, you don't share revenue numbers with summit.
Why not?
That's a good one.
I've become, yeah, I guess I'm just private about, I've always been that way, even with
storm pulse, I always share things years in hindsight, you know, in terms of financial
numbers, uh, pretty private.
I do share them with the team and we share them internally, but I think revenue numbers
are so, they're so easy to misinterpret.
Like I'm much more interested in the inputs to businesses than like the output.
And I don't want somebody to judge summit just based on this, like one number, oh, this
is your number.
You are today.
It's like, again, especially being so bottoms of the funnel focused.
It's really, I'm proud of our churn, you know, having negative churn, like I'm proud
of, you know, how much people use the product, like, so I'm sharing those numbers actually
a lot revenue.
Maybe we'll get to, because we'll get to the point where I'm like proud of that.
But we're so small right now that it's, it's kind of meaningless.
It's um, it's not really the barometer that we're using to measure our progress.
It's about to change.
But, and for listeners, you don't know churn is when people basically who are paying for
your products, stop paying for it or start paying less.
Negative churn is when your existing customers, like the amount of money you're making for
your existing company, customers every month eclipses the amount of money you're losing
from people who are churning.
And so essentially, like it's kind of a pretty sweet place to be, it's a good thing to brag
about.
Yeah, it's not easy to take away.
Yeah.
Um, you are with summit trying to build a really big company.
Uh, you're trying to like, you know, it's not good enough for you to be sort of growing
slowly to be growing massively.
Why is that?
Why set your sights that high?
What's the point?
Yeah.
And I think the more people that use the thing that I make the happier I am, like that's
pretty deep within me.
I respect the artists and the folks that could just somehow make something and then like
they sell it to one client and it's like in a house somewhere in Palm Beach, like five
people see it every year.
I just can't, I don't know how to, I don't know how to do that doesn't motivate me enough
to be perfectly honest.
So I love when people use what I've made.
I love knowing that they're enjoying it.
And so there's like a very deep intrinsic motivation in me for my creations to be used
by a lot of people.
Um, that just brings me joy, brings me a lot more satisfaction.
The other, you combine that with the fact that, you know, spreadsheets have about a
billion installs, if not regular users and, and having built something very horizontal,
it just doesn't make sense to either a try to charge a lot so that we could have, you
know, a thousand customers and still be really big, um, or be just keep it small for the
sake of, of being small.
I think the applicability is, is there.
So it's a kind of combination of two, um, exciting motivations, you know, and I brought
on investors knowing that I'm personally aligned with that.
Right.
Brings me to our next question.
Uh, you've done a lot of like bootstrapping, raising money, you know, uh, taken out sort
of loans from your co-founders or whatever the situation was, uh, what about for someone
who doesn't have this experience, like a brand new indie actor who's trying to figure out
how to navigate the fundraising sort of landscape, whether or not they should bootstrap.
What is something, I guess, what would be your advice to somebody in that situation
regarding how to think about fundraising?
Yeah.
Um, first of all, find people who are very good at it and talk to them.
I think that might require going outside of your current network or I'm not gonna say
bubble, but I'll mention it as a side note.
Like it could be a bubble, um, put yourself out there and meet people.
So like when I started fundraising, I started listening to a few people, but like a lot
of my conversations with people who had very little experience themselves.
And still to this day, I think that investors and people that raise money, the quality of
their experience and their feedback, it's varies just orders and orders of magnitude.
So, you know, the best thing you can do is find people with experience doing it and go
get your advice from them and then balance it out.
You know, maybe a constellation of people, but like the worst thing you can do is just
turn to a few people around you and say like, Hey, what should I do?
Because you're just going to get advice from people who look at, they, they literally look
at money differently than other people.
Like if you get advice from somebody who sees money as a resource to hold onto and to deploy
it very carefully, you know, that guy, you're going to get very different advice than somebody
who says, you know what, you know, what's constraining the world is like enough good
ideas.
Like we're, we're, we're constrained on ideas.
There's tons of capital out there, right?
Like you're going to get very different feedback.
So if you want to raise money, go talk to people who do it and have done it professionally
and maybe a few people that you respect that's, that's the best thing I think you do because
I can't possibly point you down a correct path in 60 seconds, but you know, put yourself
out there and find people who can.
Last question.
You mentioned earlier about a talk that basically changed perspective back in 2004.
Are there any other talks, books, blog posts, resources, things you've read or come across
that have sort of changed how you see business that other indie hackers might benefit from?
Yeah.
There are too many to mention, but I'll, I'll just recently buy us.
I'll just reach for something that I came back to recently, Jason Cohen, his Richard
King post, most people's takeaway in that post is this dilemma of, should I stay independent
or should I sell out?
That's all good.
The S curve chart that's buried in that post that shows, you know, what money does to you
as a person, I think is something that if you can internalize that, it will change your
perspective on so much.
It will help you calibrate your goals because what he basically shows is the, the reward
that you get, like the value of money is different.
So yes, the more money you have, the more valuable it is in theory, but I think most
of us are just trying to improve our lives and our lifestyles with money.
And I just love how he painted that picture, probably took him like 30 minutes in paint,
but he did the world's surface.
And if you can internalize that S curve, it can really help you calibrate your goals and
expectations of like, what do I want out of this business?
What do I want out of my next business?
And just place yourself on that chart.
I was talking to my wife the other day, went out to lunch and I was just like, you know,
I was asked, I was at a gym in 2000 and like, I want to say six and some person randomly
asked me cause they knew I was into tech.
Maybe I had like an early smartphone or something like, Hey, who would you invest in?
I'm like, Oh man, you know, I would invest in Amazon, Apple.
And like Tesla was like, somehow Tesla was either known or about to go plus something
like that.
It was like these picks and like I did.
I actually bought like what I could at the time in each of those in Tesla.
Actually shortly after they went public and you're the most depressing thing in the world.
And I'm going to come back to this chart was it made like no difference to my life whatsoever
because I had like no money to invest at the time.
Like it didn't move me up that chart, you know, like I was right, but I was invested
in the wrong thing.
And what the take of the lesson was like, you got to concentrate your bets.
If you want to move up that chart, taking the $150 or $300 I had, you know, for my piggy
bank and buying a share of Tesla, like that wasn't a concentrated bet.
Like it was, I was right.
I was right, but I wasn't concentrated enough.
And so even though it's riskier, concentrate your efforts, focus on something that if it
pays off can actually move you and then you can diversify.
So like concentrate to get wealthy, diversify to stay wealthy makes sense is the other takeaway
from that chart.
And I think most founders are sort of doing that by concentrating their bets on themselves.
Like, okay, if I start a company from zero, like that is the highest potential upside
because I'm in on the absolute ground floor.
So yeah, and I exceeds the multiplier is humongous.
I think that's, I think that's right.
And the good news is these days, at least 2021.
If you fall off that wagon, like you can get a job pretty easily.
So don't be scared.
Yeah.
My biggest takeaway from that chart, I remember it's something I've thought about in my own
life too was it's kind of like a binary thing where like all the way along that chart that
he drew, there's like, you can make more money, you can make less money, but there's a point
where you cross the line and you get into like personal financial freedom.
And that is by far the biggest thing.
Like the difference between being not free and free is way bigger than the difference
between being like a hundred millionaire and a hundred billionaire.
You know?
Yeah.
And I think that that's something people don't necessarily take into account.
And I think it comes into Greece, like you can be free from this obligation.
You can be free from this burden.
And you know, if you zoom in on the first part of that curve, you can see those degrees,
but I also think that we can become obsessed with the billions and billions and not realize
like, wait a minute, the outcome that my family needs is available to me today.
If I do this, right.
So calibrate yourself.
Cool.
All right.
Well, Matt, thanks for staying on for so long.
We've got a very cool episode with me.
Can you let listeners know where they can go to learn more about what you're up to at
summit?
Sure.
Use summit.com is the website.
Use summit is the Twitter handle.
And of course you can always find me tweeting way too much at Matt Wensing.
All right.
Thanks again, Matt.
Thanks, Kirtland.