Sameer Saran, ParkStash — Bootstrapping a Startup
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Sameer Saran was one of the very first founders Mash met when he started the incubator at San Jose State. ParkStash began as a student’s fix for the campus parking crunch. Today it’s parking management software for real estate, used by apartments, student housing, mixed-use retail sites, commercial offices and even truck parking. Sameer has been bootstrapping it for eight years, and it’s now profitable. He and Mash talk about the pivots, why Sameer won’t build anything a customer hasn’t asked for, the months during COVID when revenue went to zero, and the three things he’d tell any new founder.
This conversation has been edited and condensed.
“An Airbnb of parking”
Set the tone for us: who you are and what your company does.
I’m Sameer, the founder and CEO of ParkStash. We have parking management software for real estate. Our clients include apartments, student housing, mixed-use retail sites and commercial office spaces, all the way to truck parking. I started the company about eight years ago, after I graduated from San Jose State with my master’s.
ParkStash didn’t always start that way. What was your initial idea?
When I was a student here, it was really crazy finding parking. Even today, coming here, it’s still crazy. Walking down the driveways, I thought, maybe these people can rent out those spaces, and we have an Airbnb-of-parking model. That was the first idea, and we launched it when I was a student. Since then we’ve gone through multiple pivots. It’s a completely new platform now, and even our clients have changed. It’s more B2B.
Having run the incubator for three years, I’ve seen so many students say, “I’m going to solve the parking problem.” They last about three months and then disappear. Why can’t they solve it?
With the consumer-based model, you need enough supply. It’s really easy to think there’s so much demand — but how are you going to fill it? We first started with stadiums, and we’d only make revenue seasonally, when there were events. Then we came back to the university, but there you have to find spaces within two minutes’ walking distance, because nobody wants to walk more than two minutes. I don’t know why, but everybody wants parking close to their destination, and there’s not much supply. We had some great partnerships. But with bootstrapping, the revenue has to come, and it just wasn’t coming for us.
One quality I’ve seen in you that’s different from a lot of founders is perseverance — your willingness to push and listen and pivot, and suffer, and keep going. Where did that come from?
I don’t know where it came from, but during my school years I always participated in competitions for debating and small entrepreneurship. Many times we couldn’t build a product, or we’d fail those competitions, but we just kept going. Believe me, there have been many times when we decided, “This is not going to work out, let’s just shut it down.” But you have to see beyond that. If you keep working and find some market where that need might be fulfilled, I just go head-on at it. Once I start something, I just keep doing it.
“Why do you need money right now?”
Most founders who come to me start with the problem they think they have: “Mash, I need money.” And I say, no, you need a business, you need traction. You got some angel investment. How long did that last?
About three or four months. When we started, I’d done an internship for about nine months, so I had some money saved, and that’s what I invested into the company. Then we were winning small competitions — $5,000 — and that’s how we funded our initial marketing. But it’s insanely hard to keep doing that unless you hit the point where there’s some cash flow coming into your company. That’s the hardest part about bootstrapping.
People always come to me saying, “I’ve got this idea and I just need funding for it.” Okay — who have you talked to, and how big a need is this? “I don’t know yet, but I need money.” So why would I invest in you if you have no proof this is going to be used by someone? VC is great — I’m not against it. If you’re building a hardware startup, where there’s a lot of research involved, you definitely need money. But if it’s software, and you’re not talking to any customers, you’re not showing me revenue — then why do you need money right now?
Did you choose bootstrapping, or did you try to raise venture funding first?
Honestly, we tried to raise money after the angel investment. I think I spent about six to eight months just raising money, and the time for building the company and selling to customers was lost. At that point I decided: even investors want to see proof. Nobody’s going to give you money just like that. If I didn’t bring in revenue, I wasn’t going to go ahead and raise money. So let’s just keep bootstrapping. And now we’ve come to a point where we don’t need money.
Your challenge as a founder is to prove you’re investable — and once you get there, you ask whether you really need to take money. Say someone offered you $2 or $3 million to grow. When would you give up equity for that?
Even right now, I watch where every cent is going. So if somebody gives me $3 million, I need a real roadmap for where I’m going to spend it, because it’s someone else’s money and I need to be accountable. If I had to expand into really new markets, or create products with hardware, then yes, I would accept that money and give them a roadmap for how I’m going to use it.
“Let my customer tell me”
Early on you wanted help building out a sales team. Instead you became your own number one salesperson. How did that work out?
I’m very detail-oriented in everything I do. I wanted to know what it takes to sell to maybe 100 clients first, and then bring someone on and tell them, “This is what we need to do.” After that, if I want to build a sales team, that’s delegation, and I’m okay with that. I just wanted to experience the process myself first.
I see your LinkedIn posts — you’re getting into big accounts with multiple properties. Did doing the selling yourself make you more creative with the business?
Absolutely. It gave me one-on-one time with my customers. When I started hearing how they see our product being used in their communities, it had a drastic effect on me: “This enforcer app is actually being used every two minutes in this community, and we need to do so much more to help that.” Once I got all that feedback, I knew the relationships I was building were going to multiply. Execution and relationships have brought our company to a point where we won’t need funding, and we’re just happy growing ourselves.
You went on a road trip to meet customers all over the US, and what I got from those videos is that you really care about these people. How important is that, versus trying to pack the funnel?
It’s really important to have authentic relationships with your clients. At some point you have to ask: is my business just making me money, or is it actually impacting the ones I’m serving? You can only know that once you meet them. I met with eight or ten property managers who’ve been using our system from the beginning, and we didn’t just talk about our business. I was just understanding how they are as people. In today’s world you can’t really know what’s authentic and what’s not. People are creating apps within two days. But you can’t sell that way, especially to B2B clients. You need to understand them as people.
About three days ago I was on a call with a regional manager, and she told me we’d been phenomenal to work with — that they only want to work with people who are willing to listen and build great relationships. When you hear that from a client, you know you’ve done something great.
I tell founders they need to fall in love with somebody first — care enough about some person or market to understand them, as opposed to “I figured out how AI is going to do this,” and going around saying, “I can help you.”
When we met with these property managers, I saw how many things they’re already juggling. Now you’re bringing something on top of that. Obviously it’s going to save them time, but you’ve got to understand what their life looks like before you even sell the product. Understand the market and the customer first — and then say, “Pay me 200 bucks.”
But you did start with technology. I remember your pitch: “I have so much demand I broke the server.” When did you decide you needed to care more about the customers than about the software?
You could have the most excellent product and great demand, but until a person tells you you’re authentic and they really love your product, servers crashing wouldn’t matter. There have been times when we had bugs, and customers told us about them themselves — not “this is bad,” but “Hey, can you just fix this up for us?” That’s the kind of commitment you need from your clients. So I started focusing on that, rather than going all in on product. Now my entire team knows: nobody gives me an idea and says, “I want to build this because I think it’s good.” If you think it’s good, we’re not going to build it. Let my customer tell me that it’s great.
Even AI? Nobody’s pushing you to build agents and assistants and voice?
Believe me, my co-founder is crazy about AI. I have to tell him that just having AI wouldn’t solve this. But it has reduced our development time by almost 30 to 40%, which is great. You need experience to have AI help you, though. Otherwise it’s going to spit out code nobody understands, and it’s going to break your entire product.
For a graduating student who’s afraid AI is going to replace them, how can they look at it as opportunity instead of fear?
I don’t see it as a fear at all. I have original ideas about marketing and sales, and when I discuss them with AI, it brings me more ideas on how to sell the product. It’s not about taking my job. It’s about expanding my sales and marketing channels. It’s the same for technical development. But people who are just graduating, especially on the technical side, need to work a lot more to understand how AI actually works. They need a solid technical background, and that’s when AI is going to help them. If you’re just telling it, “Build an app for me,” it’s never going to work out. Even in jobs, people use AI to increase productivity. It’s not going to replace you if you have your originality and expertise.
I had that experience with GitHub Copilot. It wrote a function for me that worked, and then I could ask, “Why did you do it that way?” That made me better. It’s different from vibe coding something and not knowing what in the world it produced.
That’s a major drawback of non-experts just spitting out apps. There have already been many examples where people’s data was leaked online because nobody understood how the database was set up. I think a bunch of cybersecurity startups are going to come up very soon to solve these issues. We have to be careful how we use AI, and understand what it actually gave us.
“You’re not talking to any customers, you’re not showing me revenue — then why do you need money right now?”
— Sameer Saran · Inspiring Founders Podcast, Ep. 03
“Our revenue was zero”
A lot of founders who come through San Jose State don’t have generational wealth, so it’s hard to get friends and family to help. People work one, two, three jobs just to make it. You made a decision that you were going to suffer. You have a wife — I’m sure there was a moment where you sat down and said, “I’ll do this for another three weeks, and if it doesn’t work…”
She set a timeline for me during COVID. She said, “It’s going to be six months, Sameer, and if it doesn’t work out, we’ll have to think of something else.” I thank her for that, because it put more and more pressure on me to do something and bring us money. But yes, it’s huge suffering. You’ve got to have the right people with you who continuously push you and support you in those very dark times. That’s just the truth of bootstrapping.
I know B2B SaaS companies that bootstrapped to $1 million, $10 million in annual recurring revenue. It happens often. And they’re so glad they don’t have a bunch of investors looking over their stuff all the time.
That’s the pros. You have so much freedom. You’re not governed by making products that return investor money. You’re governed by the products you build for your customers, not by your investors. So many times companies pivot just because they’re not getting the returns they promised their investors. We changed our company’s trajectory within two months, and nobody was going to tell us, “What you’re doing is not right.” We control our own product and our own destiny. I always wanted that freedom — that’s why I got into entrepreneurship.
And of course we have ownership of the company. Our employees are very happy. Whatever we make, we distribute to our employees. It’s a great life once you come to a certain point.
But it’s not always like that. When were you thinking, “What in the world am I getting myself into?”
Back in 2020, when we were still doing the B2C model. We had some great partnerships with event centers and universities. And then came COVID.
Nobody’s parking.
Nobody’s parking. Our revenue was zero — literally zero. The bank balance was zero. How are you going to tell your team they’re not going to be paid for three, four, five months until we figure something out? We lost a few people during that time.
How do you tell people they can’t get paid?
We had to say that we don’t have any money. Some of the employees we were paying out of pocket. I didn’t take any salary for, I think, two or three years after we started the company. But what it teaches you is how to survive in adverse conditions. Survival is a skill not many people are learning right now. They don’t know how to stay frugal. Everybody’s salary was reduced, everybody was suffering — but then you find out who on your team is in it for the long run. The people who stayed during those times are with us today.
People need to learn how to persevere through adversity, how to be flexible and agile, how to come up with ideas instead of waiting for directions — to be entrepreneurs inside their jobs.
You have to be completely flexible and adaptable, even in your job. When you’re hit with situations where there’s no revenue, or you’re not going to be able to pay someone, you find all these hacks for how to survive. At one point we were selling sandwiches at the university. We made 100 bucks, I think. But that’s a skill you’ll carry for your life.
“You’re just going to hear a no”
Sales is a skill every founder needs and most are deathly afraid of. From the very beginning, you always said, “Stop building — go sell it, and then you’ll know.”
Because what’s going to happen anyway? You’re just going to hear a no. You learn to face rejection, and I think that’s a great skill. Now I don’t feel anything. The person said no? Great, let’s move on. Maybe it’s not the right fit for them. But you’ve got to go talk to people. So many things are virtual now, but you have to go out there and try it.
There are startups using AI to simulate customers, so founders can get to product-market fit without ever talking to one.
I didn’t know that. I don’t know how that’s going to work out. That’s crazy.
Now I bring my technical team on my sales calls, and they realize it’s not easy to sell, just like it’s not easy to code. One of my team members didn’t want to build something a customer had asked for. He thought it wasn’t what people want. So I put him on a call with the client, and the first thing she asked was, “Why can’t I download these reports from the dashboard?” I told her, “Talk to this guy — he’s responsible for it.” You can’t have that ideology in a startup. If the person who’s selling says this is what they want, this is what they want.
“Hustle needs to come with focus”
We have a generation of hustle culture. But most founders think money is the problem, and others are so enamored with technology they just want to make cool stuff. What are your top three tips for a new founder bootstrapping a startup?
First: hustle is great, but hustle needs to come with focus. There are so many distractions nowadays. When I’m doing sales or marketing, I have single-line focus: I won’t do anything else until I finish it. Your hustle can be great if you’re hustling at talking with customers. Keep doing that for a month, and then figure out what to do next. If you get distracted in between, it’s not going to work out. I’m not a good multitasker. Maybe I can handle two tasks at a time, but beyond that I mess everything up.
A friend once told me that when you multiply fractions, they just get smaller. What’s the second?
The point you raised about someone who doesn’t have generational wealth. That’s another problem to solve, which is a great problem. We didn’t have money for a long time. In that moment you have to try different ways to get money as fast as possible. It’s going to push you so hard that you’ll try some crazy hacks, and they’ll make you either sell the product or pivot your company in a different direction.
It’s the same if you’re applying for jobs. If you’re getting 100 or 150 rejections, maybe you have to try something different — develop a skill set that’s really in need right now. Maybe you didn’t learn it in four years of college, but it’s what the world wants. So always be flexible, and go the extra mile to get that money.
My brother once told me, “Never decline money.” If someone says, “I need somebody to program this for me,” you don’t say, “That’s not me.” You take the money and figure it out.
That’s like our first sale when we pivoted. We didn’t have a product. We had a slide deck, and they gave us money to build it. That’s how we sold our first pivot to the B2B market.
One of our advisers told me that’s how companies used to build products two or three decades ago, before the flood of VC money came in. Customers would pay you to build the products they want. That’s the gist of bootstrapping: you tell them, “This is what we can build, and this is what you need,” and that’s the money coming to you.
And the third?
I don’t want to sound cliché, but don’t fear rejection. For the most part, rejection has helped me a lot. When we used to knock on doors, people literally told us to go away and not come back again. If I had stopped the company at that moment, I wouldn’t be where I am today. If you get rejected, that just means you need to do something different. That’s all it means. I’ve had emails that say, “Stop, and don’t ever contact me again.” Okay. The person is going through a different phase.
I’d add perseverance. You’re going to want to quit many, many times. But the people who end up on this podcast didn’t quit.
My wife was telling me just yesterday that all the stories that finally come out are about people who didn’t give up. There’s no way out of it. You just have to keep trying. Any good company takes a decade to build — I can definitely say that. I don’t mean companies that get to $2 million and then fire all their employees the next year because nothing’s working out. Any sustainable, good company takes a decade to build.
More conversations with founders on the Inspiring Founders Podcast.