Building a Mission-Driven Company with Reuben Pressman of Presence

Courtland Allen 8s

Hello everybody. This is Courtland from indiehackers.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 Reuben Pressman, the founder of a company called Presence. Reuben came recommended to me by Rachel Carpenter. She's the CEO of a company called Intrinio 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 is awesome. But anyway, Rachel said, "Courtland, you should look into this company called Presence and talk to the founder, Reuben Pressman. He's absolutely killing it and I think he would make a great guest for the podcast." Now at that point, I had never actually heard of Presence, but the more I started reading about it and about Reuben, the more I realized that Rachel was right and that I should definitely have this guy on the podcast.

euben is an impressive figure who succeeded at doing some very difficult things. 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 from all of this from St. Petersburg, Florida. Which, if you're never heard of it, that's because it's the furthest thing away from a major tech hub. I really enjoyed listening to what Reuben had to say. I think you guys will enjoy hearing a story, too. So without further ado, let's get into it. I'm here with Reuben Pressman. Thanks for coming on the podcast, Reuben.

Reuben Pressman 1m 28s

Of course, thanks for the invite.

Courtland Allen 1m 31s

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?

Reuben Pressman 1m 38s

Basically, I've been forming a good story to go along with it. I've been programming since I was 10, so I always had a very big background in technology and always been passionate about how technology can help solve either very small or very big problems. It's become so accessible that there's lots of resources available to make it possible to build something.

I've also kind of labeled myself as a compulsive problem solver. If something's broken, I must fix it. Those few things go very nicely together. Typically those things align with the passion that I have or something I'm very involved with or I've experienced myself. For Presence, that was my experience in student government in my undergrad and as staff in student affairs.

From a student government perspective, most people don't realize that student governments typically have a lot of authority and autonomy at their universities and colleges. They're typically in charge of allocating millions of dollars potentially. A large school like University of Central Florida by us here, their student government's in charge of allocating $25 million a year. That causes...

Courtland Allen 2m 44s

Whoa.

Reuben Pressman 2m 45s

Yeah, exactly.

Courtland Allen 2m 45s

I had no idea.

Reuben Pressman 2m 47s

Yup. That causes all kinds of interesting problems and issues and difficulties 'cause you basically have college students which at heart are still learning and gaining real world experiences. But they could be freshmen and they can be sophomores, so they have a high school diploma and some experience interacting with people but they're responsible for helping allocate that much money.

That money's supposed to go towards interactive events, experiences, initiatives, departments and services on campuses in a division called Student Affairs. That's basically the other side of the institution besides Academic Affairs. So think everything with the student union, any type of intramural, all the student club and organizations, all of residential life, all of that.

Courtland Allen 3m 32s

How do you guys at Presence fit into this giant mass of Student Affairs being in charge of millions of dollars?

Reuben Pressman 3m 39s

What we focus and while there's companies like Blackboard and other learning management systems and tools from an academic side, there's a huge amount of data lacking on the Student Affairs side. We realized that data was the core problem to everything from getting students involved to allocating something like $25 million a year to retain students. As well as assessing and understanding what's going on and reporting some of those data that's now starting to be required more often for institutions. We focus on the data problem there.

I always start that way just as a just 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? That's really where our focus is. That's where we differ a lot from others in the market, in the industry, especially for education is because our education is so big and vast that you can obviously roll something out that's helpful and people use it, but we're focused on solving really important problems. We always start there for the focus. The way we solve it is that deeper problem is data.

We started with a way to swipe and collect the information of what students are doing in 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 could participate on the campus outside the classroom. So, anything from like I said, res life to student union events to intramurals, to student club organizations, to activities board and student government and health and wellness, and tutoring, and it keeps going on.

Courtland Allen 5m 6s

That sounds vast. I have a lot of questions to ask that I'm sure we'll get into, but how do you go about building something like that and selling it?

Reuben Pressman 5m 13s

It gets crazy. 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. This really turned into an entire platform. Everything from a ton of backend tools that allows organizations to stay organized with all of their memberships, 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 and Typeform. We do all the stuff they do but we add a whole bunch of other logic and conditional logic and integrations with other products and process management 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. With the mobile where we're tracking, we use some other cool features like polls, live polls, signing with your finger waivers. Then really where our bread and butter is is taking all the tracking information we have.

All the information structured from this specific events and things they're participating in and we combine that with the student information system data that the institutions already have. So things like age, gender, race, and major in classes, 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 real time see the types of trends and behaviors students are doing and how that relates to financial allocation, the retention correlations, and we top it off with mobile app and website that's custom branded, that's automatically built from all of the experiences the institution's creating for their students, and 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, and 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 and about 35 different states and three different countries.

Courtland Allen 7m 29s

Wow, is that three years since you started Presence as a whole or three years since that last particular product that you're talking about?

Reuben Pressman 7m 37s

No, so three years is since we launched that full, since we launched the MVP of the product that we had already done some iterations with some close campuses with and kind of beta tested.

Courtland Allen 7m 49s

When was your original start date? When did you first start working on Presence?

Reuben Pressman 7m 53s

Late 2012 is when we really got the team together and said all right, let's do this.

Courtland Allen 8m 0s

Okay, so it's been about four to four and a half years? Just to give the listeners some context, I won't 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.

Reuben Pressman 8m 15s

We have basically double institutions every year. We've also closed to double employees every year. Investment's almost tend to run and about the same as well. 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. Then we've raised just under two million of fundings so far.

Courtland Allen 8m 43s

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. We've all been through it in some way or another. And 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. 'Cause 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?

Reuben Pressman 9m 30s

To me, it's got 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 everyday and put 110% into that, but it's also extremely hard to come in everyday just because you're passionate at 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 the viable piece of that can be a lot easier. But it's a huge balance.

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 the incorrect problems being framed and focused on. So I always come out with 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 listening to Indie Hackers, they know what that means. For those that don't, it's minimum viable product. It's those 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 they earn for that. That's our focus with everything. 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 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.

The reason it took us so long to launch an initial product or I guess not take 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 the 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 and all learning we could, and we still do, it's just at a different scale to assess and decide what to be added in the platform, what to build, what problems to solve, all of that.

Courtland Allen 11m 52s

That's a lot of work. 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 is 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 is what makes your products 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. 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?

Reuben Pressman 12m 38s

That's a great question. No, I'm always envious of those that sell a venture, they profit from a venture, and are able to say, I'm going to go ahead and really do this next one right. It's like, okay, cool, great. That sounds really convenient. No. I'm kind of in the middle of that and very fortunate to have decided to start learning how to 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 have the same vision in mind. One wanted to be a full time artist and that's even more difficult in my opinion, but 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. We basically worked double time, built up a lot of savings. 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 it got to a point where I felt comfortable enough with what I saved up and eased out of that and transitioned the time, went to full time with this right around the same time we started closing our first one or two schools. Once we have that, we were at the point where I could go to some investors that I'd already been talking to and I have all kinds of philosophy around how that process can work as well.

Courtland Allen 14m 0s

You like consulted your way into bootstrapping your way into raising money.

Reuben Pressman 14m 4s

Basically, yeah. We ended up getting those first few customers on board. Got the investors to buy in once we had that. I've raised just under 100k. That's our first seed round which brought myself and three others on full time to take a stab at doing what we need to do.

Courtland Allen 14m 22s

That's so unheard of. I live in downtown San Francisco and there is no way under 100k would get four people on full time.

Reuben Pressman 14m 32s

That's the biggest difference with location too and everyone loves being in San Francisco 'cause likewise you could walk into or get meetings at 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. If you don't have one of the very few connections to resources here, it's close to impossible. 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 or four years ago, now we've started seeing a lot more increase 'cause we've had a few big wins here. The only reason I was able to raise money is 'cause I interned with the only tech accelerator we had here when I was in school. I sat on 15 different nonprofit boards. Just after the year I graduated, I got involved with every startup there was and just got to know everyone. I'm maybe one of 15 to 20 people that have had it easier raising any type of funding here.

Courtland Allen 15m 41s

So you just networked the shit out of it, basically.

Reuben Pressman 15m 43s

Yeah, I did.

Courtland Allen 15m 44s

Would you consider yourself an extrovert?

Reuben Pressman 15m 46s

Oh yeah, I rate like 98% extrovert. I have a hard time, and actually I know I always like to point out, extroverted versus introverted is not how outgoing or any of that you are, it's where you get your energy from. Because I'm so extroverted, if I'm alone, I get absolutely nothing done.

Courtland Allen 16m 5s

You have to network. You don't have an option.

Reuben Pressman 16m 6s

I have to be around people. Like if I ever come to the office and no one's here, I'd probably get half the work done if at least someone was like upstairs with me or around the space with me. So there's pros and cons.

Courtland Allen 16m 18s

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?

Reuben Pressman 16m 28s

It's actually pretty close to what we launched. I definitely wanted 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 a list of students coming in, connect it with the demographics we knew they already had with a really simple event thing. It was basically current organization, what the organization's name was literally what the form was. Then current event with a few details about it. Then, boom, there you go. Now you can go in the app and you can put in the details for the event that you just made and start swiping people in. That's all it was.

Courtland Allen 17m 7s

What IDs were these? Student IDs or driver's licenses?

Reuben Pressman 17m 11s

The student IDs that they already have. For us, because it's mainly institutions, working with such a huge number of students, accessibility, all that stuff, we of course would love to do things like iBeacons and all kind of different stuff. While we're doing our idea on these projects and things like you have digital IDs that you can use, and a big selling point to these institutions is not changing the behavior of the students and not require them to do anything different to get involved. They all have to carry an ID. If you don't have, we just input that type of ID that you have.

Courtland Allen 17m 45s

It sounds like you're aware of kind of what institutions needed early on. I think one of the bigger questions a lot of people have when they're trying to figure out what to work on is, 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. It sounds like you erred towards the former where you had experience inside these campus groups and students 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?

Reuben Pressman 18m 15s

I think you definitely need both. I went to school for entrepreneurship so I had a lot of these stuff in my head and they are concepts that I think are pretty intuitive but having it spelled out and talking about theory in entrepreneurship is a whole another level. One of the questions that I always ask of entrepreneurs that others always asked of me early is why are you the person to do this? That comes from an expertise side. Like, why are you going to be successful over somebody else doing the same thing? It's less like, what's stopping Google from doing this? Those to me are always useless questions.

The important question from the expertise level is why are you the person who'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. You 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. For me, it's havingthat 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 when you're not interested in it. I think those things work very much hand in hand.

Courtland Allen 19m 39s

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. 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 education 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?

Reuben Pressman 20m 26s

That's an awesome question. 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 be able to travel 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.

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 give great understanding of what other people are going through. Then start looking at deep understandings of those problems and being able to then look at the possible solutions for those. I phrased 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's low, retention's hard, assessment's difficult, allocating financials is hard. The underlying deep problem in multiple layers is missing and inability to understand data. For these other problems, it's realizing that the problems you typically see or feel are usually caused by something deeper.

When you can solve that, then you're solving those and many other problems and you're hitting that in deeper value there, and it gives you a different frame to approach what you're building. 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 plain that all of those understanding and 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 your point still be wrong.

Courtland Allen 22m 28s

Yeah, I really like what you said about there always being multiple solutions to a problem because I talked 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. When in reality, if you see people paying for a solution to a problem, that's validation. That tells you that 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. That might be you 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. 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?

Reuben Pressman 23m 23s

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. Education, as you mentioned even earlier, touches so many pieces of society. It's directly impacting every type of class or person and helping level the playing field. It's providing a future and bigger opportunities for people to change the way their lives are.

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. It not only build 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. Especially in this kind of political climate.

It also helps from a workforce standpoint. We know with jobs and how important that is, we know about the skills gaps, 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 be able to really make a dent on that is getting more educated, more focused people that are going to be able to help and solve that jobs and workforce problem for everybody. I see this as 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 of solving.

Courtland Allen 24m 57s

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. Then the people that I talk to on Indie 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.

Reuben Pressman 25m 26s

They are. That's the issue with the valley and like Austin and Boston and Chicago, and all those many tech cities is that even the investors in those cities are starting to branch out. One of our investors is 500 Startups in the valley. They've only recently or a lot other firms started trying to invest in companies outside of bay areas in California, and it's because they know everyone over there is extremely biased and they're focused on only the problems they can experience.

I mean Jack Dorsey for example was known for riding the bus between work and the two companies he's trying to run because it's the only way he can stay connected to anything in the real world without having something digital filtering or showing him that. Being in a place that isn't just hardcore tech and whatever you could ever want in the palm of your hand any time everyday delivered to you, and I think it's a huge benefit. Absolutely.

Courtland Allen 26m 23s

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 their company's goals and your mission, 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.

What's your take on what it means to be a mission-driven company in 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?

Reuben Pressman 26m 54s

I think culture is extremely important with that, so I don't think it's just monetary. Especially for how generation and where a lot of business is shifting and where large corporations and people are having a hard time in is that people care about the mission and what's happening a lot more than they used to and you 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.

For us, what we're doing is a huge win. From a recruitment standpoint, all the people on our team, they're are saying, well, I've always wanted to do something with 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. It almost helps us filter out people 'cause, 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. If that's not there, it's almost a straight no from a hire standpoint and 95% of time, candidates are applying, they're applying because they want to make an impact of what we're doing it.

Courtland Allen 28m 14s

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 and align incentives and cleverly.

Reuben Pressman 28m 26s

Can't have culture that way. Not sustainable culture for sure. That's a huge thing for us. Every single person, except our software developers are either former student affairs professionals or former student leaders at the company.

Courtland Allen 28m 43s

Okay, so that's how you deal 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's 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 course correct if you're not?

Reuben Pressman 29m 17s

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. Then further may tell somebody else how amazing it is. To me, it's that from a customer standpoint to know we're actually helping and making an impact and seeing the data for these customers fixing the things that they came to us for.

And because we have been doing this for too long because the closing cycle's crazy for education and there's a lot of barriers to entry and time to implementation for a software is leveled, 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 on our site that really showcase these things. I don't have any really great anecdotes from a customer's specific like data increase, but it's seeing those referrals coming through is kind of the most heartwarming thing that I experience something 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 literally falling in love with this. I think some of my favorite quotes I hear employees say is I could never go back to working to anything else besides a company like this. Because it's just so different and so impactful and the way we do things is just so much more practical than the principle of things. It's typical startup culture that you hear about, but, I think adding up mission-driven adds a whole other level of that.

We do, we still do with 22 employees, all hands meetings for like 20 minutes every Monday afternoon after lunch. I just stood there and kind of look at everybody and it's just amazing that everyone's here because of what we've made together and what I had a dream of one night or experienced, and everyone's like, this is what we want to do to help people. I think that's really heartwarming on the employment side.

Obviously, the investor side is awesome. We have a lot of extremely reputable investors and even education related investors that are truly believing in what we're doing and where we're going, and I think that's really cool from all angles.

Kind of another relation I think people can see and go back into kind of one of the things you we're talking about with building value as well as making an impact, and I think you can look at these benefits although minus some of the culture issues that they've had and 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 of business model for making impact.

HR's 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 government filing and everything. I think they took an approach to say, we're going to 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 and take advantage of people for it, and we're going to make it free.

So they took this model of saying, we're going to give you free HR software and do everything you could ever imagine and make it really easy. And then we're going to make our money doing it, helping selling health insurance when you're ready for it. They got big, they grew extremely fast. At one point, they were the fastest growing company in the country, I believe, and raised up to $20 million or $10 million or something like nine months after launching, and then they're rolling like two million through that and raise another like 60.

They just have been crushing it. It was because they were onboarding customers because they've built a great product that 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 it. They just made the same broker fee as every other insurance company made.

Courtland Allen 32m 57s

They figured out a very clever way to still be profitable as a company while making things way easier and cheaper for everybody else.

Reuben Pressman 33m 4s

Exactly, and I kind of call it the redirect. It's, we're going to solve an issue for these people, but we're going to make our value from somebody else, right?

Courtland Allen 33m 10s

Is that something that you think you need to build in and design into your company before you even start or is this something you could figure out on the way?

Reuben Pressman 33m 17s

I absolutely think you can figure 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 and you have those in mind. It's something that we've done and that we've considered. 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.

Courtland Allen 33m 39s

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. Who was working with you when you got your first schools onboarded?

Reuben Pressman 33m 50s

Honestly, when we got those first schools, it was like in the middle of raising that little seed round and bringing other employees on. It's really just me and his name's Andy. He's 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, what was our first beta customer, 'cause he was a student government president, and as he was graduated, I was like, yo, come do this with me. I already got the product built. We've got schools that are interested. Just come on and help me get some more schools. And so he did that and he's been with me ever since. Yeah, it was just him and I basically for a while. We closed that little round, launched it, brought three people on.

Courtland Allen 34m 32s

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, 'cause that's a lot to handle.

Reuben Pressman 34m 41s

I have no idea how we did it. I try to stay very organized. I try to keep a task list. Because there's so much going on, you know, the big tips that I've always had is writing down everything down. Not write, but I'd put on the temporary notes or reminders, or whatever tool I'm using that week. 'Cause for me it's being able to stay focused in the moment.

So if other ideas come up, I don't ignore them. I don't put them away. I'd write them down and be right back to what I was doing. By keeping everything at least written down on a list anywhere, I don't stress about remembering. I don't stress about getting to it. And I'm able to prioritize those when I have plenty of time to do that, and I could focus on a specific thing to do at that time. For me, it's less balancing and it's more focusing on the one particular thing that's the most important at that time. There's always something.

Courtland Allen 35m 33s

What about your time investment back then? Were you working eight hours a day or were you working 16 hours a day or do you remember?

Reuben Pressman 35m 40s

I haven't worked a day in my life that wasn't typically close to 16 hours. Means something. I'm lucky to where I can usually get and feel just fine getting about three to five hours of sleep at night. It's a huge benefit there. I get that and I'm full of energy the entire rest of the day. I have no problem with that. Typically, I'm most energetic at the office. I have a huge, very fortunate there, biologically, I guess.

Courtland Allen 36m 11s

You're the second person I've talked to who is extremely prolific and productive and who also sleeps like four hours at night.

Reuben Pressman 36m 18s

But I think a lot of that also comes from the passion side. I'm like, I wake up and like, holy shit, I got to get in the office and get a bunch of stuff done because that's what I want to do. That is to me what really even makes that more possible is your energy comes from loving what you do all day. It's very helpful. Back to the question you have, and this was like priorities, 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 help me prioritize and understand and be more deliberate about how I spend my time. And even now, we're constantly changing priorities when little things shift and change and, like my CTO came to us and we have a couple of priorities we're working on and was like, hey listen Mike, I know this was important but because this, this, and this, that's we're considering now. He's like, yeah, switched them right around the afternoon.

It was a big change for us. We took people off projects, put different people on different projects instantly. And everyone was like, cool, and that's just normal for us.

Courtland Allen 37m 21s

What kind of breakdown did you have early on in terms of developing the product versus talking to customers? 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?

Reuben Pressman 37m 33s

No, we upfront talked to people before we built anything. We basically brought a concept. I pitched without demo to people and talked through things with people we knew, people we didn't know, people we have interest to, whatever it took to get in front of our potential customers, so we're learning about the problems they have and what we knew we wanted to solve, and how we wanted to do that.

We spent some good time doing that. At the same time almost, just building kind of the start of the MVP but keeping it flexible enough to where if we learned something groundbreaking, we could make that change. Then it kind of shifted once we had what we felt was enough input to solely building the initial product. And actually we started talking to investors as early as possible. I can explain why later. 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 and understanding using it and making sure it was something that did solve those problems. Then we of course went from there and then was able to launch the actual MVP that people would pay for.

Courtland Allen 38m 36s

Do you remember if there are any specific assumptions that you guys had early on that got completely shut down once you started talking to people?

Reuben Pressman 38m 43s

We were charging too little.

Courtland Allen 38m 46s

That's a common one.

Reuben Pressman 38m 47s

We would come in and I want to be like no contract month to month, no worries, super easy. They're like, can we pay yearly? Also, like, this thing's really cheap.

Are you sure you can do all this for this cost? One year minimum. Three years if you want it. And double our pricing right off the bat. 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. 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.

Courtland Allen 39m 33s

How long after you've kind of got through this talking phase and into 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?

Reuben Pressman 39m 42s

It took us unfortunately a solid eight to nine months. That was a lot longer than we had hoped for and what it probably should have taken. But because we were part time, it took that long still. We were actually working with some really difficult technology with the analog card readers, and because they're using headphone jack and we're using… Credit cards are done fairly well, but student IDs are very cheap and that technology is really interesting 'cause we're literally taking a magnetic strip that basically has three different tracks of encoded information, similar to like what 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 the sound wave and tones into the device, and we had to decode the amplitudes and the frequencies of that sound wave on the server and send that down from zeroes and ones to translate into what was actually on that card. That whole process took a ton of time. Square doesn't but some of the other platforms make you press start, swipe the card, and you can't stop and 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. It 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 all that different stuff. There was a lot of development tech to had to go into that piece, but then, I'm also huge on user interface. One of our biggest selling points in education that there's alot of legacy stuff out there and people that are just building random things don't focus on. The user interface took a lot of testing, a lot of feedback on that. It's the details that really took the longest for us.

Courtland Allen 41m 28s

Were you the one coding all these or was your partner helping you?

Reuben Pressman 41m 32s

I had a partner that I contracted with initially to build, he built most of the backend, the web services and stuff. I built all the front end and did the design. Then I had another friend that owned an agency focus on the mobile initially.

Courtland Allen 41m 46s

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?

Reuben Pressman 42m 13s

No, I felt I've been good at at delegating is it's come down to priorities. I always loved economics classes solely because of the cost benefit model and saying, let the people that are really great at something focus on the things that they're really great at and everybody else focus on the things they are great at. We even take that from a product standpoint. There's thousands of things we can add on to the product to make it better. There's also people we start competing with and people doing other things.

When I have conversations about partnerships with those companies or with someone with that, I felt one of the biggest lines I say is, we're going to focus on what we're really good at and we're going to let them focus on what they're really good at, and you're going to get two amazing products instead of one that just does everything okay. I think it's the same thing from delegation standpoint is let everyone do the things that they're good at and you're going to end up with a great product.

For a lot of people that haven't built things before especially other people who haven't had a lot of experience doing that for other people, it's hard. It's your baby, you've dreamt of it. It's your life, whatever you want to say it is. It's hard to let that go for a lot of people. I think once they do, it's great. I take the same approach even for management.

We hire a lot of people that have not necessarily managed or worked with other people directly in the way that we do internally with the company, and I enjoy helping people understand how important it is to delegate and let things go and do that. I love seeing that shift in their mind. As soon as they see delegating starting to work, it's all they do and it gets really easy once you make that jump.

Courtland Allen 43m 39s

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 this somebody else? How do they vet them? Et cetera.

Reuben Pressman 43m 56s

I was going to say to answer your immediate question with delegation is just do it. You're always going to get surprised. Worst case, it doesn't work out and you're back where you started. Great. You were already working on something else anyway and you can already get back to it. From a finding, it's always a big question especially for first time entrepreneurs.

I did it through networking. 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 in St. Petersburg doesn't get referred to meet with me within the first few meetings they take with people. Just because I've really focused on getting to know everyone there is to know. Making impact with helping people here. I think that's something that you can't really price or understand that value of and something I still have a really great passion for.

I now work really closely with our economic development and our mayor and the people in the city here to help bring other companies here and help them align the resources they might have to help other entrepreneurs here. I don't think I can ever undervalue networking in that sense, not like going to things and handing your business card out, please. But it's getting and knowing what all the process is so that when it's time for you to want to go do something, you could put a Facebook post out for example and say, hey, I'm building a project, who wants to work on 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 is their thing, they don't want to do that, they can always go to meetups, especially developer meetups and just hang out and see what people are working on and just make a couple of friends that have the ability to build things. Listen, whether it's an investor, whether it's an employee, a cofounder, a customer, all of those people get on board because of inspiration and your ability to inspire them. They get onboard 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 and helps you empathize with it. It helps you believe in it. That can't ever be undervalued either. I guess that's my advise for finding, especially with technical cofounders.

Courtland Allen 46m 7s

We're rapidly approaching the end of our conversation here. I want to wrap up by just discussing the psychology behind being a founder. People who've listened to a few episodes of this podcast know this one of my favorite topics of conversation just because of how underrated 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?

Reuben Pressman 46m 40s

Absolutely. It's constant. As cliche as it is, it's a roller coaster. For me, it's for every, the things that make the ups and the wins so upsetting is because there were losses. Like if you just won everyday, it'd be just as boring. The fact is that those losses make the wins that much better. We talk about these sales, because sales is like the immediate closest to what it's like to run a company with wins and losses. When we're training and we're talking about like nos and getting rejected in sales is we talk about a yes to no ratio, and how there's always a certain amount of nos, you're going to need it to get to the yes.

I look at it the same way from a wins and losses standpoint day to day is that for every loss or for every how many losses, I know there's going to be a win at some point. And if those losses keeps stacking up, it's only going to be that many more wins that are going to happen after. It's knowing that that ratio is there to help get through it. But I also love the losses inside because those are new problems that I can focus on or learn from and be able to make sure it don't happen again. To me, 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 expected. The losses, although I know they're coming and are around, are the things that are challenging, that you can train the opportunities, and that help you grow. 'Cause honestly, you don't really grow from wins.

Courtland Allen 48m 20s

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.

Reuben Pressman 48m 30s

You're really good at summing things up.

Courtland Allen 48m 34s

I think that's a smart strategy and I think one of the challenges of working in 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 wracking when you're pouring so much heart and effort into each decision. This is especially true early on. 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 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. 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?

Reuben Pressman 49m 40s

I try to be as open and transparent and honest as possible. I'm a big fan of that and I don't think there's even 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 and helps them understand that the things they are doing make an impact overall, which is by far the most motivating thing for employees.

For investors, they're invested and all they want to do is help. They want to make sure that what they're there for is both protecting their investment but also making it worth more if they can help get through something. I mean, I have different people I go to for different problems and issues, depending on what they are. If they are technical, I have technical people. If they're emotional, it might be family or friends or whatever that may be.

Courtland Allen 50m 29s

Do you find it's difficult living in a place that's not a tech hub to find people who can relate to the issues that you have and the challenges that you're overcoming?

Reuben Pressman 50m 36s

No, although I do feel like if I had to put tiers to it we're pretty close to a second tier tech city. 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 unless, well, no I guess, they're pretty close now. But it's going to be rare that I'm going to connect with someone that I know that's also working in a startup at any place that you go to as over here for something like San Francisco.

But no, we live in like one of obviously the most technological time there is. I have Slack groups. I have forums. I have direct connections. I have 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 happened and I do not let them get me down in any way. For me, it's like I personally haven't had a need for very strong emotional support with things. It's more or less just getting 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 big philosophy personally that I basically go on with the idea that nobody knows what they're doing. And I found it to be true almost 100% of the time. When you take that approach especially when you're working on something, if you're truly working on something new and innovative, there really isn't anyone that knows what they're doing. You're making it up as you go. And as long as you realize that, then you're only just trying to get to the right success story.

I don't remember who said it or what it was, but somebody famous said I didn't fail, I only found a whole bunch of ways not to do it on the way to doing it, right? I think all those things kind of mix in to the idea that 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 is important to have a need for. It's more the technical pieces or someone to bounce ideas off of.

Courtland Allen 52m 38s

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 Indie Hackers and then at some point during the process, people started asking me for advice on how to do things and I'm like, 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 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?

Reuben Pressman 53m 12s

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. If it's like a couple of questions or something here and there, or whatever. I always love like the, hey, can I buy you coffee? Can I buy you a drink? Hey, I'd love to take you to lunch, it'd be quick. Lunch is always one of my favorites 'cause everyone's got to eat.

But if it's online, it's just like, hey, I got a couple of quick questions. I'm trying to get through this. You've really inspired me on how this, this, and this worked. And I don't think I've ever not had anybody respond with something helpful. I even get hit up quite often and even though I have less than zero time like everybody else these days, I still find the time to throw a couple of answers and tips out to help people.

So, I think as long as you're honest and open about that and upfront, I think people are more than willing to help typically.

Courtland Allen 54m 4s

That's a perfect answer. I'm going to start forwarding all of my emails to Reuben Pressman and let you take care of them. Tricked you. But anyway Reuben, 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?

Reuben Pressman 54m 23s

Man, I just took down my personal website 'cause it's been like five years since I've updated it. So reubenpressman.com just goes to my LinkedIn now, how boring. Basically I am the company at this point. So I don't even have a personal email anymore. It's just my company email. Everything I do with my life basically goes into Presence.io. That's what we're working on.

We have a sweet blog that talks about new employees being hired and things we're doing. We try to share some startup knowledge. We've been doing a lot more around culture and inclusivity 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 @ReubenPressman. I have a Facebook, although I typically try to keep that more personal, but it is not private. I kind of chime in and post little updates about things that are important. But almost all of it's company related at this point. I'm kind of boring outside of that.

Courtland Allen 55m 14s

You're a walking talking company.

Reuben Pressman 55m 16s

That's basically it. I play some sports in the evenings to make sure I stay exercised and fit, and that's about it.

Courtland Allen 55m 22s

Awesome. Well, thanks so much for coming on the podcast, Reuben.

Reuben Pressman 55m 25s

Of course, thanks so much for having me. I greatly appreciate it. And I hope everyone enjoyed at least one thing I said.

Courtland Allen 55m 33s

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