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Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe

Transcribed podcasts: 277
Time transcribed: 11d 5h 6m 45s

This graph shows how many times the word ______ has been mentioned throughout the history of the program.

Hello, everybody.
This is Cortland from NDHackers.com, where I talk to the founders of profitable internet
businesses and I try to get a sense of how they got to where they are now and what goes
on behind the scenes, with the goal being that the rest of us can learn from their example.
Today I'm talking to Ruben Pressman, the founder of a company called Presence.
Ruben came recommended to me by Rachel Carpenter.
She's the CEO of a company called Entrenio and I had her on the podcast a few weeks back.
If you haven't listened to that episode, by the way, I recommend that you do.
Rachel's awesome.
But anyway, Rachel said, Cortland, you should look into this company called Presence and
talk to the founder, Ruben Pressman.
He's absolutely killing it and I think he would make a great guest for the podcast.
Now at that point, I'd never actually heard of Presence, but the more I started reading
about it and about Ruben, the more I realized that Rachel was right and that I should definitely
have this guy on the podcast.
Ruben is an impressive figure who's succeeded at doing some very difficult things and that
ranges anywhere from learning to do enterprise sales to gigantic school systems to building
a mission driven company where the ideals and goals come first, which is much easier
said than done and doing all of this from St. Petersburg, Florida, which if you've never
heard of it, that's because it's the furthest thing away from a major tech hub.
I really enjoy listening to what Ruben had to say.
I think you guys will enjoy hearing his story too.
So without further ado, let's get into it.
I'm here with Ruben Pressman.
Thanks for coming on the podcast, Ruben.
Of course.
Thanks for the invite.
So you're the CEO of Presence, a tech company in the education space.
Can you give us a sense of how you got started as an entrepreneur and specifically with Presence?
Basically I've been a good story to go along with it.
I've been programming since I was 10, so I've always had a very big background in technology
and always been passionate about how this technology can help solve either very small
or very big problems, and it's become so accessible that there's lots of resources
available to make it possible to build something, and I've also kind of labeled myself as a
compulsive problem solver.
If something's broken, I must fix it, and those two things go very nicely together,
and typically those things align with a passion that I have or something I'm very involved
with or have experienced myself, and for Presence, that was my experience in student government,
in my undergrad, and a staff in student affairs, and from a student government perspective,
most people don't realize, but student governments typically have a lot of authority and autonomy
at universities and colleges, and they're typically in charge of allocating millions
of dollars potentially.
At a large school like the University of Central Florida buying us here, there are student
governments in charge of allocating $25 million a year, and that causes all kinds of interest
and interesting problems and issues and difficulties, because you basically have college students
which at heart are still learning and getting real world experiences, but they could be
freshmen, they could be sophomores, so they really have a high school diploma and some
experience interacting with people, but they're responsible for helping allocate that much
money, and that money is supposed to go towards interactive events, experiences, initiatives,
departments, and services on campuses in a division called student affairs, and it's
basically the other side of the institution besides academic affairs, so think everything
with a student union, any type of intermural, all the student collective organizations,
all of residential life, all of that.
So how do you guys at Presence fit into this giant mass of student affairs being in charge
of millions of dollars?
What we focus on, and while there's companies like Blackboard and other learning management
systems and tools from an academic side, there is a huge amount of data lacking on the student
affairs side, and we realize that data was the core problem to everything from getting
students involved to allocating something like $25 million a year to retaining students,
as well as assessing and understanding what's going on and reporting some of this data that's
now starting to be required more often for institutions.
So we focused on the data problem there, and I always start that way just as a kind of
side tip when I'm pitching something like this, or any company, and when I work with
other entrepreneurs is you should be solving problems, right?
And that's really where our focus is, and that's where we differ a lot from others in
the marketing industry, especially for education, is because education is so big and fast that
you can obviously roll something out that's helpful and people will use it, but we're
focused on solving really important problems, so we always start there from a focus, and
the way we solve it is that deeper problem is data.
So we started with the way to swipe and collect the information of what students are doing
and all of these things to begin with.
So we have a device just like Square, and it plugs into iOS and Android phones and tablets,
and lets you swipe students into every single thing they can participate on the campus outside
the classroom.
So anything from, like I said, Res Life to student union events to your murals to student
club organizations to activities board and student government and health and wellness
and tutoring, and it keeps going on.
Yeah, that sounds vast, and I have a lot of questions to ask that I'm sure we'll get into
about how you go about building something like that and selling it.
It gets crazy.
So we start there.
If we can collect this data, we can do so much with it and help them solve those and
a bunch of other problems.
And it's really turned into an entire platform, everything from a ton of back end tools that
allow organizations to stay organized with all of their membership, their rosters, their
documents, their history, their communication, we have an entire event management system
that's basically like Eventbrite, but for your campus and your organizations that has
custom approval workflows built in and integrates with all the space reservation tools they
use.
And then we have a form builder, if anyone's familiar with Wufoo or Google Forms or Typeform,
we do all the stuff they do, but we add a whole bunch of other logic and conditional
logic and integrations and other products and process management and workflow with those
that allow them to really replace any paper form and process they have on campus with
information in our system integrated with the other pieces.
And on the mobile where we're tracking, we use some other cool features like polls, live
polls, signing with your finger waivers.
And then really where our bread and butter is, is taking all the tracking information
we have, all the information structured for the specific events and things that participated
in.
And we combine that with the student information system data that the institutions already
have.
So things like age and gender and race and major and class and so many more, as many
as 80 different types of attributes about students, we import in and then give them
real time super great visual reports and analytics that allow them to in real time see the types
of trends and behaviors students are doing, how that relates to financial allocation,
the retention correlations.
And then we top all that off with mobile app and a website that's custom branded, that's
automatically built from all of the experiences the institutions creating for their students.
So now they have one location to go to instead of emails and flyers around campus, word of
mouth and social media and all these different places, they have one spot they know they
can go to get the most updated information about what's going on.
So we had that and we launched it back in May of 2014 after spending almost a year building
initial product, testing it, working with some very close institutions with it, iterating
it and getting it to a point that made sense to start talking more broadly and publicly
about it.
So just over three years, we're now at over 110 institutions in about 35 different states
in three different countries.
Wow.
Is that three years since you started presence as a whole or three years since that last
particular product that you were talking about?
No.
So three years is since we launched the MVP of the product that we had already done some
iterations with some close campuses with and beta tested.
When was your original start date?
When did you first start working on presence?
Late 2012 is when we really got the team together and said, all right, let's do this.
So it's been about four, four and a half years.
And just to give the listeners some context, I want to ask you to reveal your revenue numbers,
but can you give us some measure of your progress so far and where you're at as a company in
terms of employee sizes and you said you're at 110 institutions?
We have basically double institutions every year or so.
We've also close to double employees every year or so.
Investments almost tend to run about the same as well.
So we're at 22 employees now, we're on track to be about 30 by the end of the year, we're
at 100, just over 110 institutions, again, in 35 different states and a few different
countries.
And then we've raised just under 2 million of funding so far.
You mentioned earlier that education is vast.
And I think everyone would agree with that.
It's also fraught with problems and everybody has different opinions on how to fix them.
I think partly because the educational system affects all of us, like we've all been through
it in some way or another.
And it also in part because it's so complex and opaque that anybody can come up with a
solution and it's hard to see why it won't work.
So it just feels good tossing out solutions.
How did you personally decide which problems to tackle?
Because there's so many factors that can play into that.
You can decide based on your own personal passions and mission.
You can decide based on what's the most viable way to make your business work because at
the end of the day, you need to generate sales.
What led you to decide that you're going to go into the student affairs part of education
versus other parts?
Yeah, to me, it's going to be a balance of those things.
You can't go into something just because it's viable.
It's going to be hard to wake up every day and put 110% of that.
But it's also extremely hard to come in every day just because you're passionate about something
and not get anywhere because it's not viable.
So I think there's going to be a pretty strong balance between those.
I think especially with how some of the larger cities like fund companies and focus on growth,
they care more about the passion than they do the viable piece of it because they know
that if they can build an audience around something, adding products onto that or adding
a viable piece of that can be a lot easier.
But it's a huge balance and for me to focus on student affairs was because of my passion
with that, because of my direct experience and knowledge and what I believe was a very
unique viewpoint and where I saw a lot of things being missed and their incorrect problems
being framed and focused on.
So I always come out these types of problems and even picking problems very philosophically
and then figuring out the most simple and that MVP is that big word, which I'm sure
if anyone's listed as indie hackers, they know what that means.
But for those that don't, it's a minimum viable product.
It's the simplest product you can create that still holds value and solves a problem
for a person that would be willing to at least exchange some amount of value there for that.
And that's our focus with everything and whether it's how we chose to start or whether it's
how we do it now, I have a huge product roadmap both in my head and obviously written down
of where we love to see everything go, but that constantly gets impacted by our existing
customers and by our prospects and helps us weigh and prioritize where we want to go and
where they feel they need to go.
So the reason it took us so long to launch that initial product, or I guess that takes
so long at all, to me that's exactly how it should be, is there was a lot of research
to be done.
We didn't want our biases and experiences to run the entire initial products.
We talked to as many people as we could.
We iterated the product.
We watched people use it.
I mean, even after we launched our first few paying customers, I personally was at every
single one of those institutions when they were using the product for months and longer,
even in the first year to watch how they were using it, make sure it made sense, ask them
tons of questions in all the learning we could, and we still do, it's just at a different
scale to assess and decide what to be adding the platform, what to build, what problems
to solve, all of that.
That's a lot of work.
And I really like what you said about not wanting to inject your own biases and personal
opinions into the product because you're not representative of how everybody's going to
use it.
So you need to spend like those months on campus watching people use it and tweaking
the models that you guys have for what makes your product useful.
I think that's something that, number one, a lot of people underestimate the importance
of.
It's very easy to get in your own head and think that, okay, your vision for the user
interface for your product and the features that are important are going to be what everybody
else finds useful.
And number two, I think a lot of people don't have the time to spend months or years talking
to people and tweaking something without actually getting a product out the door that makes
money.
How did you guys fund your early efforts in doing this?
Did you raise money right off the bat or were you riding off of the profits of some earlier
venture?
That's a great question.
No, I'm always envious of those that, you know, sell a venture, get profits from a venture
and are able to say, well, I'm going to go ahead and really do this next one, right?
And it's like, okay, cool, great.
That sounds really convenient.
No.
So I am kind of in the middle of that and very fortunate to have decided to start learning
kind of program and also do design at a professional level very early on.
And I've kind of always had side projects that I was helping others build.
And as I graduated and wanted to transition to my company at some point knew that I wanted
to stay flexible.
So I didn't go get a job.
I started an agency with a couple of friends that had the same vision in mind.
One was, you know, wanted to be a full-time artist and that's even more difficult in my
opinion, but it was a great illustrator and graphic designer as well.
So we kind of teamed up and said, let's help other people build their products and get
their stuff out.
And we basically worked double time, built up a lot of savings.
And kind of because we have flexible hours, we were working part-time on our own things
as well as working together on the other people's and then got to a point where I felt comfortable
enough with what I had saved up and eased out of that and transition the time into full
time with this right around the same time we started closing our first one or two schools.
And once we had that, we were at the point where I could go to some investors that I
had already been talking to, and I have all kinds of philosophy around how that process
can work as well.
You like consulted your way into bootstrapping your way into raising money.
Basically, yeah.
And we ended up getting those first few customers on board, got the investors to buy in once
we had that and I raised, it was under $100K, it was our first seed round, which brought
myself and three others on full time to take a stab at doing what we needed to do.
That's so unheard of and I live in downtown San Francisco and there's no way under $100K
would get four people on full time.
Well, that's the biggest difference with location too and everyone loves being in San Francisco
because likewise, you could walk into or get meetings out much more easily with the huge
amount of investors that are out there or get connections to other tech companies or
whatever that is.
The difference here is costs are lower, but opportunities are much, much lower exponentially
compared to the cost of living differences.
So if you don't have one of the very few connections to resources here, it's close to impossible
and most of my friends that run other companies end up leaving, it's getting a lot better
now.
I used to say that more like three, four years ago.
Now we've started seeing a lot more increase because we've had a few big wins here, but
the only reason I was able to raise money is because I interned with the only tech accelerator
we had here when I was in school.
I sat on 15 different nonprofit boards after the year I graduated.
I got involved with every startup there was and just got to know everyone and I'm maybe
one of 15 to 20 people that have had it easier raising any type of funding here.
So you just networked the shit out of it basically.
Yeah, I did.
Would you consider yourself an extrovert?
Oh yeah, I rate like 98% extrovert.
I have a hard time and actually I always like to point out extrovert versus introvert is
not how outgoing or any of that you are is where you get your energy from, right?
Because I'm so extroverted, if I'm alone, I get absolutely nothing done.
You have to network.
You don't have an option.
I have to be around people.
Like if I ever come in the office and no one's here, I probably get half the work done if
at least someone was like up in the upstairs with me or around the space with me.
So there's pros and cons.
So you mentioned you said a few words earlier about a minimum viable product.
What was the minimum viable product that you had in mind right when you started working
on presence?
Yeah, and it's actually pretty close to what we launched and I definitely want to bring
that up earlier.
So I'm glad you mentioned it.
The original ideas was let's swipe IDs on mobile phones and give people lists of students
coming in connected with the demographics we knew they already had with like a really
simple event thing.
So it was basically create an organization, what's the organization's name was literally
what the form was and then create an event with a few details about it and then boom,
there you go.
Now you can go in the app and you can, you know, put in the details for the event you
did that you just made and start swiping people in and that's all it was.
And what IDs are these?
Like student IDs or driver's licenses?
They're the student IDs that they already have.
Yeah, no.
So for us, because of being an institution, working with such a huge range of students,
accessibility, all of that stuff, we of course would love to do things like eye beacons and
auditory frequencies and all kinds of different stuff and while we're doing our ID on those
projects and things like we have digital IDs that you can use, the big selling point to
the institutions is not changing the behavior of their students and not requiring them to
do anything different to get involved.
So they all have to carry an ID they don't have work, we just integrate with that type
of ID they didn't have.
It sounds like you're aware of kind of what institutions needed early on and I think one
of the bigger questions a lot of people have when they're trying to figure out what to
work on is, okay, do I need to have expertise in a particular area before I start working
on a business there or should I just do whatever I'm most passionate about even if I don't
necessarily know?
And it sounds like you aired towards the former where you had had experience inside these
campus groups and student affairs and so you knew kind of what problems they were facing
and what types of solutions they were more likely or less likely to adopt.
Is that accurate to say?
Yeah, I think you definitely need both.
I mean, and I went to school for entrepreneurship so I had a lot of this stuff to drill into
my head and there are concepts that I think are pretty intuitive but having it spelled
out and talking about theory and entrepreneurship is a whole other level so one of the questions
that I always ask with the entrepreneurs and that others always ask me early is, why are
you the person to do this, right?
And that comes from an expertise side.
Why are you going to be successful where somebody else is doing the same thing, right?
And it's less like, well, what's something Google for doing this?
And those to me are always useless questions but the important question from an expertise
level is, why are you the person that's going to be the most successful building this?
And there should be some type of level of knowledge or something unique that you see
in the market differently than anybody else.
And still, we have competitors in the market that were much bigger than us that have now
started trying to copy what we're doing.
We have other startups that are coming after us trying to do it but because they don't
approach it with the same philosophy, they're just looking at the features we have, people
don't understand it.
It doesn't make sense and they're not able to connect it.
And for me, it's having that deep understanding of that market which I think you can really
only get if you're passionate about it because it's so hard to get ingrained and go deep
into a topic where you're not interested in it.
So I think those things were very much hand in hand.
Yeah, it's funny that you mentioned competitors just copying your features without understanding
the underlying reasons of why you're actually building those features.
So they're copying you blind and it always reminds me of situations where you see two
companies that don't even know what they're doing copying each other.
A lot of people working on coming up with an idea run into this problem where they can't
identify any particular area of expertise to draw from.
Let me put you on the spot here and ask you to imagine a hypothetical world in which all
of your knowledge and memory about education has been completely wiped.
So you're not allowed to start a startup in the educational space here because you don't
know anything about it.
What process would you go through to decide what kind of company you want to build and
do you think you would take the time to develop expertise in an area first or would you just
dive right in?
That's an awesome question and I feel like I'm already prepped for that answer because
I'm definitely a serial entrepreneur.
I don't know how long I'll be doing this one for but because I'm that way I'm always thinking
about what could be next.
And so I'll approach this the same way I would when I get to that point and it would be my
plan is to throw myself in as many new and complicated experiences as I can.
I want to be able to start, I want to go to the trial of the world but through third world
countries and through really big problems that I try to move away from these first world
problems and things that just help people that don't really need help overall.
So for me it would be getting involved and putting myself in experiences that make me
uncomfortable that get me the ability to learn things and empathize and get a great understanding
of what other people are going through and then start looking at deep understandings
of those problems and being able to then look at the possible solutions for those.
And I phrase that very carefully because when I say deep problems I mean that most problems
are very surface level and even big problems are.
So I can relate that to what we're doing now.
The surface level problems for what we do are student engagement is low, retention is
hard, assessment is difficult, and financial is hard but the underlying deep problem multiple
layers is missing and ability to understand data.
So for these other problems it's realizing that the problems you typically see or feel
are usually caused by something deeper and when you can solve that then you're solving
those and many other problems and you're hitting that kind of deeper value there and it gives
you a different frame to approach what you're building.
And I phrase solutions plural because there's always, I don't care what you say, always
multiple ways to solve any problem and it's playing with all of those, understanding they're
talking to your audience, getting input, testing them out to get to the one that's going to
make the most sense but also realizing that you could get to a point and still be wrong.
Yeah, I really like what you said about there always being multiple solutions to a problem
because I talk to so many people who I think have it mixed up.
They're afraid to build something that solves a problem that's already been solved because
they think well then nobody will have a reason to use my product.
And in reality if you see people paying for a solution to a problem that's validation.
That tells you that hey this problem is painful enough for people to pay for a solution.
Just having that validation can save you years of heartache caused by building a solution
to a problem that nobody cares about.
So I definitely don't think you should run from already solved problems but instead you
should find a way to solve those problems in your own unique way that differentiates
you from competitors.
So that might be you're solving it better than them or faster or cheaper or you're targeting
a different niche.
The other thing you said that I really liked was that you want to get away from solving
surface level first world problems.
And I'm curious how does that play into what you're doing at presence and how do you assess
whether or not you're actually fulfilling your mission?
Yeah, absolutely.
I think education is one of the biggest problems worldwide.
We're obviously focused on the US because it's what we know and where we're starting
but like I mentioned we're in other countries as well.
We have a school that's using us in Pakistan for example.
So for me I mean education as you mentioned even earlier touches so many pieces of society.
It's directly impacting every type of class of person and helping level the playing field.
It's providing a future and bigger opportunities for people to change the way their lives are.
And to me that's impacting everything from how educated our entire country is and how
we can solve other problems because we have a more educated workforce or society that
not only builds hard skills that relate to those directly but soft skills like social
skills that help with communication period that help people have a better understanding
of each other and especially in this kind of political climate.
But it also helps from a workforce standpoint and we know with jobs and how important that
is.
We know about the skills gap.
We know about all of the things that other problems that exist like jobs in the country
and even the world that education is the only way that you're going to be able to really
make a dent on that.
It's getting more educated, more focused people that are going to be able to help and solve
that jobs and workforce problem for everybody.
So ICU is being again kind of another deeper underlying problem with many other bigger
ones in the country and the world that we're focusing in our unique way on solving.
Yeah and I think it kind of highlights dichotomy between some of the high growth super highly
funded companies you see coming out of typically places like Silicon Valley and then the people
that I talk to on ND Hackers who are more often than not not in some sort of tech hub.
They're all over the place in Pennsylvania, Florida, Ohio and there's a part of me that
hopes that the people in these places that are more typical of what regular people in
the world are going through are better positioned to solve real problems.
They are.
That's the issue with the Valley and like Austin and Boston and Chicago and all those
main tech cities is that even the investors in those cities are starting to branch out.
So one of our investors is 500 startups in the Valley.
They've only recently and a lot of other funds started trying to invest in companies outside
of the Bay Area.
It's in California and it's because they know everyone over there is extremely biased and
they're focused on all the problems they can experience.
I mean Jack Dorsey for example was known for riding the bus between work and the two companies
is trying to run because it's the only way they can stay connected to anything in the
real world without having to have a digital filter and they're showing you that.
So yeah being in a place that isn't just hardcore tech and whatever you could ever want in the
palm of your hand at any time every day delivered to you and I think is a huge benefit absolutely.
Another challenge I think with running a mission driven company is being able to hire skilled
employees who are on the same page as your mission because everybody's at least somewhat
self-interested and no matter how much they align with your company's goals or your mission
if they don't feel like they're valued highly enough or paid well enough then they won't
take the job or at least they won't stay for very long.
So what's your take on what it means to be a mission driven company and essentially a
capital driven society and how do you go about aligning your company's goals with your own
personal goals and the personal goals and incentives of your employees?
I think culture is extremely important with that so I don't think it's just monetary and
especially for our generation and where a lot of business is shifting and where large
corporations and people are having a hard time meeting is that people care about the
mission and what's happening a lot more than they used to and we know a lot of other important
things like room for growth and obviously some type of minimum but I see people a lot
more forgiving the monetary value for the other things and for us what we're doing is
a huge win.
I can from a recruitment standpoint I'll hit people up where people on our team there said
well I've always wanted to do something in education there's not very many markets that
or industries that people are going to say that for so I think it's actually a huge win
when it comes to building great culture with great people that do want to be an impactful
company and it almost helps us build throughout people because I'm going to give this away
but I don't really like to.
One of the biggest things I look for in interviews and that we look for is a passion for what
we're doing over anything else and if that's not there it's almost a straight no from a
higher standpoint and 95% of the time candidates that are applying are applying because they
want to make an impact of what we're doing.
So you're basically putting the filter before people join and you want to find people who
are already on the same page as you rather than having like a post hoc okay everybody's
here now we're going to enforce this culture on you or we're going to try to align incentives
and cleverly.
No culture that way.
Yeah no not sustainable culture for sure.
Yeah no I mean that's a huge thing for us and every single person except our software
developers are either former student affairs professionals or former student leaders at
the company.
Okay so that's how you do it with your employees.
What about you personally as a founder?
When you go home at night what is it that makes you feel good about how your business
is doing and how does that compare to the metrics that you track on a day to day basis
because I know that for any company especially one with investors there are certain metrics
and numbers that people want to see that don't always align with how things are going on
the ground in terms of whether or not your business is making a positive impact in people's
day to day lives.
What do you look at to determine if you're doing a good job and to kind of of course
correct if you're not?
I think one of the coolest things is having our customers tell other people they have
to use this and those people buy in and do that and then further they tell somebody else
how amazing it is and to me there's like it's that from a customer standpoint to know we're
actually helping to make an impact and seeing the data for these customers fixing the things
that they can do us for and because we haven't been doing this for too long because the closing
cycle is crazy for education and there's a lot of terms to entry and time and implementation
for a software at this level we're just now starting to get some really cool data out
of customers and we're starting to do case studies and things that we're going to be
putting out on our site that really showcase these things so I don't have any really great
data and it does from a customer specific like data increase but it's seeing those referrals
coming through is like kind of like the most heartwarming thing I think that I experienced
from being related on the customer side on the employment side it's that people are moving
across the country and taking these opportunities to work with us and then like literally falling
in love with this and I think some of my favorite quotes I hear from employees say is I could
never go back to working like to anything else besides a company like this because it's
just so different and so impactful and you know the way we do things it's just so much
more practical than the principle of things and it's you know it's typical like startup
culture that you hear about but I think adding that mission driven as a home they're allowed
with that so we do we still do with 22 employees all hands meetings for like 20 minutes every
Monday afternoon after lunch and I just sit there and kind of look at everybody and it's
just amazing everyone's here because of what we've made together and what I you know had
a dream of one-nighter experienced and everyone's like this is what we want to do to help people
and it's I think that's what we are warming on the employment side and obviously the investors
that's awesome we have a lot of extremely reputable investors and even education related
investors that are truly believing in what we're doing and what we're going and I think
that's really cool from all angles another relation I think people can can see and go
back into kind of one of the things you were talking about with building value as well
as making an impact and I think you can look at Zenefits although you know minus some of
the culture issues that they've had in some of the shakeups but if you look at their business
model it's been very interesting I've always brought them up as a great example business
model for making impact and HR has always been this obnoxious annoying thing and a huge
barrier to entry and sometimes massive problem and even causing failure for companies to
manage and understand and especially when it comes to the government finals and everything
so I think they they took an approach to say we're gonna make an impact to make it easier
for startups and for companies to manage this stuff and get rid of all these people that
charge me too much for it and take advantage of people for it and we're gonna make it free
so they took this model and said we're gonna get free HR software to do everything you
could ever imagine and make it really easy and then we're gonna make our money doing
it helping selling health insurance when you're ready for it right so they got big they grew
extremely fast at one point they were the fastest growing company in the country I believe
they raised like 20 million or like 10 million dollars or something like nine months after
launching and then they were only like 2 million through that and raised another like 60 and
they just they just have been crushing it and it was because they were onboarding customers
because they built a great product it didn't cost anything and they were making a ton of
money because when they were ready for benefits they were going through them and they didn't
charge for those they just made the same broker fees everybody up every other insurance company
made yeah they figured out like a very clever way to still be profitable as a company while
making things way easier and cheaper for everybody else exactly and I kind of call it the redirect
it's we're gonna solve an issue for these people but we're gonna make our value for
somebody else right is that something that you think you need to build in and design into your
company before you even start or is it something you could figure out on the way I absolutely
think you can you can figure it out on the way I think there's a ton of benefit of spending the
little amount of time it might take to think about all the possibilities of ways you could do it
you have those in mind and it's something that we've done and that we've considered and I think
especially from an investment angle those are things that investors want to know that you're
thinking about and that you are capable of so let's let's rewind back to the beginning again
and let's talk about the first few schools that you onboarded because there weren't many of you
was it was he was working with you when you got your first schools on boarded honestly when you
got those first schools was like in the middle of like raising that that little seed round and
bringing the other employees out so it's really just me and his name is Andy he's our he's our
now our director of campus development so basically director of sales VP of sales all
kind of the same thing he had been working with me for months and months just on sweat equity but
was our first beta customer because he was a student ever president and as a graduate I was
like yo like come do this with me I've already got the product bill we've got schools that are
interested just you know come on and help me get some more schools and so he did that and he's
been with me ever since but yeah it's just him and I basically for a while we close that little round
launched it brought three people up give us a sense of how you're juggling all of these tasks
of finding somebody to work with building the product selling people on the product as well
raising money because it's a lot to handle yeah I have no idea how I did it it's I try to stay
very organized I try to keep the task list because there's so much going on you know the big tips
that I've always had is writing everything down not right but I put it all in a trello or you
know it's our reminders or whatever tool I'm using that week because for me it's being able to stay
focused in the moment so if if other ideas come up I don't ignore them I don't come away I write
them down and write back to what I was doing so by keeping everything at least written down on the
list anywhere I don't stress about remembering that I don't stress about getting to it and I'm
able to prioritize those when I plan time to do that and I can focus on a specific thing I'm going
to do at the time so for me it's less balancing and it's more focusing on the one particular
thing that's the most important at that at that time and there's always something and what about
your your time investment back then were you working eight hours a day were you working 16
hours a day or do you do you remember I haven't worked a day in my life that wasn't typically
close to 16 hours in something so I I'm lucky where I can I can usually get and feel just fine
getting about three or five hours of sleep a night wow benefit there um I'm and I get that and I'm
full of energy the entire rest of the day I have no problem with that typically the most energetic
at the office so I have a huge very fortunate there um biologically I guess you're the second
person that I've talked to who is extremely prolific and productive and who also sleeps
like four hours a day yeah but I think a lot of that also comes from the passion side right I'm
I'm like I wake up I'm like holy shit I gotta get in the office and get a bunch of stuff done
because that's what I want to do and that is to me what really makes that even more possible
right is is your energy comes from loving what you do all day um so it's very helpful um
but back to the kind of question you have on the specific priorities it's it's being able to
prioritize understand the importance of things I hate staying surface level so I always go deeper
with why things are important I always ask multiple levels of why and that helped me prioritize and
understand and be more deliberate about how I spend my time um and even now we're constantly
changing priorities when when little things shift and change and you know like my CTO came to us and
you know we have a couple priorities we're working on he's like hey listen like I know this was more
important but because this is this let's reconsider and I was like yeah switching right around and it
was a big change for us we we took people off projects put different people on different
projects instantly and everyone was like cool and that's just normal for us what kind of breakdown
did you have early on in terms of developing the product versus talking to customers I mean did you
spend were you switching off every other day or did you spend some dedicated months of just building
what you thought people would use so no we upfront talked to people before we built anything we
basically brought a concept and pitched without demo to people and talked through things with
people we knew we didn't know people we got interest to whatever it took to get in front
of our potential customers to learn about the problems they had and what we what we knew we
wanted to solve um and how we wanted to do that so we spent some good time doing that and and you
know at the same time almost as building kind of just started the MVP was keeping it flexible
enough to where we learned something groundbreaking you could make that change then kind of shifted
once we had it what we felt was enough input to slowly building the initial product and
actually relate this back we started talking to investors as early as possible um and I can
explain why later and then once we had a product we started trying to get people to use it didn't
charge anything it was more valuable for us at that point to see them using it understand them
using it making sure it was something that did solve those problems and then you know we of course
didn't really look from there and then were able was able to launch the actual MVP that people would
pay for do you remember if there were any specific assumptions that you guys had early on that got
completely shut down once you started talking to people yeah we were charging too little that's a
common one yeah so we would we would come in and I wanted to be like the no contract month to month
no worries super easy and they're like can we pay you really also like this seems really cheap are
you sure you can do all this for this cost and you're like what okay yeah no totally okay yeah
well one year minimum three years if you want it and doubled our pricing right off the bat
and they were totally right because we've since continued to raise pricing to be able to offer
the level of support which is I love to brag under a minute response time from our customer service
team and it's because we're able to they're able to afford a slightly higher price that allows us to
provide the best solution and the best service with that that we can
right and how long after you you kind of got through this talking phase and end of the product
building phase how long did it take you to build a product that you're able to go to customers with
and say will you buy this it took us unfortunately like a solid like eight to nine months and that
was a lot longer than we had hoped forward and what it probably should have taken but because
we were part time it took that long still and we were actually working with some really difficult
technology with the analog car readers and because they're using headphone jacks and we're using
like credit cards are done fairly well but like student IDs are very cheap and that technology is
really interesting because we're literally taking a magnetic strip that basically has three different
tracks of encoded information similar like a record has and all that card reader is a needle
just like a record and it's being moved back and forth and recording the sound which is playing
as a sound wave and tones into the device and then we have to decode the amplitudes and frequencies
of that sound waves on the server and send that down from zeros and ones to translate into what
was actually on that card so that whole process took a ton of time like we you know square doesn't
but some of the other platforms make you press start swipe the card to hit stop because it's
recording audio so we're doing this this always listening so you can just keep swiping cards we're
doing a lot of background stuff there was just a lot of actually advanced technology that we had
to build in because we wanted to use readers we could get out for free that they were analog and
they were ubiquitous between devices and and all that different stuff so there was a lot of
development um tech that had to go into that piece but then i'm also huge on user interface
one of our biggest study points in education with the ton of legacy stuff out there and people that
are just building random things um don't focus on so the user interface took a lot i want to
be testing a lot of feedback on that so it's the details that really took the longest for us
and were you the one coding all this or was your partner helping you
i had a partner that i contracted with initially to bill he built most of the back end the web
services and stuff um i built all the front end and designed and then i had another friend that
owned an agency focused on the mobile initially one of the challenges that a lot of entrepreneurs
struggle with is finding the right divide between doing things themselves and hiring capable people
that they can delegate tasks to i know i personally struggle with this a lot and i suspect that it's
a bigger challenge for developer founders just because as a developer you have a lot more
opportunities to do things yourself looking back on the early stages of presence were there any
areas where you perhaps should have done more delegation and less handling the task yourself
no i thought that always made it delegating it's come down to priority it's it's you know i always
love economics classes solely because of the cost benefit model and saying you know what the people
that are really great at something focus on the things that they're really great at and then
everybody else focus on the things they're great at we even take that from a product standpoint
there's thousands of things we get out onto the products make it better but there's also people
we start competing with and people doing other things and when i have conversations about
partnerships with those companies or with schools with that i bought one of the biggest lines i say
is we're going to focus on what we're really good at we're going to let them focus on what they're
really good at you're going to get two amazing products instead of one that just does everything
okay and i think it's the same thing from a delegation standpoint is you know let everyone
do the things that you do and you're going to end up with a great product and i think you know for
a lot of people that haven't built things before especially with other people or have a lot of
experience doing that for other people it's hard it's your baby you've dreamt of it you know it's
your it's your life whatever you want to say it is it's hard to let that go for a lot of people
and i think once they do it's great and i take the same approach even for management we hire a
lot of people that not you know have not necessarily managed their work with other people directly in
a way that we do internally with the company and i enjoy helping people understand how important
is to delegate and let things go and and you know do that and i love seeing that shift in their
mind that as soon as they see delegating starting to work it's all they do and it gets really easy
once you make that jump so you're a veteran at delegating what tips do you have for somebody
who's not a veteran somebody listening in who might be time constrained or might not have the
appropriate skills to do everything themselves and needs to work with somebody else how do they go
about finding with somebody else how do they vet them etc yeah i was gonna say to answer your
immediate question with delegation is just do it you're gonna you're always gonna get surprised
and yeah worst case it doesn't work out and you're back where you started great um you were already
working on something else anyway and you can already get back to it so from a finding that's
always a big question especially for like first time entrepreneurs and i did it through networking
you know i try to stay as humble as i can but it's just a good example i did everything possible
locally and it's extremely rare someone talented that comes around st petersburg doesn't get referred
to meet with me within the first like few meetings they take with people just because i've really
focused on getting to know everyone there is to know making an impact and helping people here
and i think that's something that you can't really price or understand the value of and something
that's still a really big passion for i now work really closely with like our economic development
and our mayor and the people in the city here to help bring other companies here and help them
align the the resources they might have to help on their entrepreneurs here i think only can everyone
undervalue networking in in that sense not like going to things and handing your business card out
please um but uh just getting to know everyone all the processes so that when it's time for you to
want to go do something is you can you can put a facebook post out for example say hey i'm going to
build a project who wants to work on it and you just get it you get to the point where you have
to choose the person not necessarily find them but for people that don't feel networking um is
is their thing they don't want to do that you can always go to meetups especially developer meetups
and just hang out and see what people are working on and just make a couple friends that have the
ability to build things and listen whether it's an investor whether it's an employee a co-founder a
customer all of those people get on board because of inspiration and your ability to inspire them
and they get on board through inspiration through stories that's the best way to inspire anybody
again why i started this entire podcast through a story is because it helps you understand it helps
you empathize with it it helps you believe in it and uh that can't ever be undervalued either um
so i guess that's my advice for finding especially technical co-founders so we're rapidly approaching
the end of our conversation here but i want to wrap up by just discussing the psychology behind
being a founder and people who've listened to a few episodes of this podcast know this is one of
my favorite topics of conversation just because of how underrated uh founder psychology is in
determining how likely we are to succeed with our businesses you seem to be somebody who's
driven a lot by your passion for the work that you do for its own sake but at the same time there
have to come days where you wake up feeling a little bit more pessimistic or dejected than usual
about the outlook for your business what do you do in those situations how do you handle it
yeah absolutely it's constant um as cliche as it is it's a roller coaster um but uh for me it's
you know for every the things that make the ups and the wins so exciting is because there were
losses like if you just won every day it could just as boring the fact is that you know those
those losses make the wins that much better and we talk about it in sales because sales is like
the immediate closest to like what it's like to run a company with wins and losses and when we're
training and we're talking about um like knows and getting rejected in sales is we talk about
a yes to no ratio and how there's always a certain amount of knows you're going to need it to get to
a yes and i look at it the same way from a wins and losses standpoint day to day is that you know
for every loss or forever how many losses i know there's going to be a win at some point and if
those losses keep stacking up it's only going to be that many more wins that are going to happen
after and it's it's knowing that um that that that ratio is there to get you know to help get through
it but i also love the losses and you know inside because those are new problems that i can focus on
or learn from and be able to make sure don't happen again um so to me that's that's that's
almost more exciting than the wins the wins are something that i'm already working hard to get
and it's kind of even subconsciously expecting the losses although i know they're coming in or
around are the things that are challenging that are you can turn the opportunities and that help
you grow um because honestly you don't really grow from wins so you're taking like a holistic view
basically to prevent yourself from being isolated and focusing way too much on one particular loss
you look at the entire record and say okay this is just one part of a bigger story yeah you're
really great at summing things up i think that's a smart strategy and i think one of the challenges
of working on a startup is that you don't always have access to all of the information you don't
know what the long-term results of every decision that you make is going to be which can be nerve
racking when you're pouring so much heart and effort into each decision this is especially true
early on so in the absence of having any real signal what you do is you zoom in on individual
events and you blow them up in size to way bigger than they really are for example if something goes
wrong if you miss out on an important sale or your site goes down or your launch doesn't go as well
as you'd hoped it's super easy to magnify stuff like this and let it get into your head and get
into a situation where you're super dejected and demotivated and you want to quit when in reality
this is just one isolated event that is only a small part of the overall life of your company
and i think what amplifies this is that as a founder there aren't very many people who share
the same roles and the same cares that you do to the same degree that you do so it can be hard to
find people to talk to who can actually empathize with what you're going through who do you rely on
if anybody to talk about the challenges that you face as a founder yeah i try to be as open
transparent and honest as possible i'm a big fan of that and i don't think there's ever been
anything that's come out of that negatively i think keeping employees in the loop of what's
going on helps them stay motivated helps them understand that the things they're doing making
impact overall which is by far the most motivating thing for employees and you know for investors
they're invested all they want to do is help they they want to make sure that what they're
there for is both protecting their investment but also making it worth more or if they can help get
through something yeah i mean i have different people i go to for different problems and issues
depending on what they are if they're technical i have technical people if they're you know
emotional it might be family or friends or whatever that be do you find it's difficult
living in a place that's not a tech hub to find people who can relate to the to the issues that
you have and the challenges that you're overcoming no although i do feel like if i had to put tears
to it we're pretty close to a second tier tech city so i mean we have hundreds of startups in
the bay area here so although they're not like super dense and i can't walk to a coffee shop
and as well you know i guess i can pretty close to you know but you know it's going to be rare that
i'm going to connect with someone that i know that's also working on a startup at any place
that you go to you know as i'm here for something like san francisco um but no i mean we live in
like one of the obviously the most technological time there is i have slack groups i have forums
i have direct connections i've got friends with hundreds and hundreds of founders nationwide
worldwide that i can reach out to and talk with but i think more than anything it's like i'm in
this and i know those things happen and i do not let them get me down in any way and for me it's
like i don't i don't i personally haven't had a need for very strong emotional support with things
it's more or less just hitting people up and seeing if i can't figure out a solution to it
how somebody might have approached it on their own but i have a pretty pretty big philosophy
uh personally that i i basically go along with the idea that nobody knows what they're doing
and i found it to be true almost 100 of the time and when you take that approach especially when
you're working on something if you're truly working on something new and innovative there isn't anyone
that knows what they're doing you're making it up as you go and and as long as you realize that then
you know you're only just trying to get to the right success point and i don't remember who said
it or what it was but somebody famous said you know i didn't fail i i only found a whole bunch
of ways not to do it on the way to doing it right so i think all those things kind of mix into the
idea that you know you have to set your own expectations if you understand things can go wrong
then i feel like when those things do go wrong it's not as impactful and the emotional side of things
are it's important to have a need for it's more the technical pieces or someone about ideas off of
i think that's perfectly stated especially the fact that nobody really knows what they're doing
i certainly didn't know what i was doing before i started with nd hackers and then
at some point during the process people started asking me for advice for how to do things i don't
know i don't know why you're asking me i have no idea to end on i would love to get your thoughts
on and hear your advice for people on how to effectively reach out to people to ask them for
advice and help because you mentioned that if you weren't able to solve a problem you know you
would find someone else who did and pick their brain what's an effective way to go about doing
that and then actually get people to respond to you honestly i think people love helping other
people as long as it's not like hey i need a bunch of hours of your time is you know if it's
like a couple questions or something here to there or whatever you know i always love like the hey
can i buy you a coffee can i buy you a drink you know hey i'd love to take you to lunch really
quick lunch is always one of my favorites because everyone's got to eat but if it's online it's just
like hey i got a couple quick questions i'm trying to figure out how to do it i'm trying to get
through this you really inspire me on how this this and this worked you know and i don't think
i've ever not had anybody respond to something helpful and i even get hit up quite often and
you know even though i have less than zero time like everybody else these days i still find the
time to throw a couple answers and tips out uh to help people so i think as long as you're
um honest and um you know open about that and up front i think people are more than willing to help
typically that is a perfect answer i'm going to start forwarding all of my emails straight to
ruben pressman let you take care of them tricked you well anyway ruben it was great to have you
on the podcast you're dishing out some serious startup knowledge where can people go online to
find out more about you and what you're doing man i just took down my personal website because it's
been like five years since i've updated it so ruben pressman.com just goes to my linkedin now
how boring so no i mean basically i am the company at this point so um i don't even have a personal
email anymore it's just my company email and everything i do with my life basically goes into
presence.io so that's what we're working on we have a sweet blog that talks about new employees
we hire new things we're doing we try to share some startup knowledge we've been doing a lot more
around culture and inclusivity in our in our blog which is becoming a huge focus for us i'm very
inactive on social media i do have a twitter so you can follow me at ruben pressman and i have a
facebook although i typically try to keep that more personal but it is not private and i kind of
chime in i post little updates about things that are important but almost all of its company related
to this point so i'm kind of boring outside of that you're a walking talking company that's
basically it i play some sports in the evenings to make sure i stay exercised and fit and that's
about it awesome well thanks so much for coming on the podcast ruben of course thanks so much for
having me i greatly appreciate it and i hope everybody enjoyed at least one thing i said
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