Starting another company is like asking a seasoned marathon runner to lace up their shoes, turn around and tackle another 26.2 miles — it takes an extraordinary level of determination and perseverance. While there is clarity and wisdom that comes from the experience of crossing the finish line before, that doesn’t mean the path ahead will be easy.
While some of the challenges that plague the first-time founder — like co-founder conflicts and hiring missteps — might be easier to sidestep, others — like the struggle to find product-market fit — are likely to still rear their ugly heads. Then there’s the added difficulty that the repeat founder’s perspective may be clouded by past priorities and assumptions that no longer serve them. Here’s how Dennis Pilarinos, two-time founder of Buddybuild and now Unblocked, likes to analogize it:
“Let’s pretend we’re in an office right now. If we shut off all the lights and had to walk through here, we’d probably bump into the desks and chairs, right? Because we don’t know where they are,” Pilarnos says. “But if we’ve been in here before and we shut off the lights, we probably have some sense for where things are. So the second time, you roughly know where the furniture is, but you’ll still bonk your toe on a few things.”
There is a wealth of advice and resources available for first-time founders tackling the daunting challenge of building a company from scratch. We’ve even recently unpacked the subject ourselves on the Review. But we know the road also looks a little different the second time around, so for the next part in this series, we’ve asked a select cohort of some of the smartest repeat founders we know to share their most useful pieces of advice for starting a company again.
Their insights, compiled below, offer a unique window into navigating the psychological and operational challenges of starting up — all over again. While this advice is from the second-time founder lens, there’s still plenty of wisdom to go around for first-timers, too. Let’s dive in.
ON GETTING INTO THE RIGHT MINDSET:
Every repeat founder’s reasons for starting something new are different. For some, it’s the allure of getting a successful exit or reaching a higher mountaintop. For others, they just can’t stay away from the rush of building something new from scratch. But what most founders don’t anticipate are the profound impact to your mindset that comes with doing it all over again.
When every milestone you reach in your company journey (closing a seed round, hiring your first engineer, closing your 100th customer) is no longer shiny and new, it can be harder to pull from that well of motivation that kept you going the first time. In this section, seasoned founders divulge what baggage sat alongside them as they slid into the driver’s seat for the second time, along with tactics for how they coped.
Don’t let a past venture cast a shadow on your next one.
Bob Moore is a rare breed. A three-time founder and the current CEO at Crossbeam, Moore has scaled and sold companies in 2008, 2016 and is running the ship at his latest company since 2018.
Moore has shared his sage advice from his three different ventures on the Review before, but there’s one tidbit we think is particularly relevant to starting over again, which is not to let the outcome of your last venture weigh too heavily on your new one.
“When you get beat, when your strategies aren’t working, when you have to do layoffs, when you announce a modest acquisition — it’s easy to hang your head,” says Moore. “It’s not exactly confidence-inspiring to see your first venture go somewhat quietly into the night. After the modest outcome of my first startup, I was questioning whether I could ever raise money again.”
“What was I going to say? ‘Hey, I’m the guy who pounded his chest before, trust me this time?’ It also gets personal, fast. You think, ‘Have I wasted these years of my life?’ or ‘Is my career as an entrepreneur over?’” he says.
As a first-time founder, it’s easy to believe that the only return on investment you get from your startup is the proceeds from your exit. “Turns out the experience was the real payoff,” says Moore.
It wasn’t until I was building my second company that I realized the upside of falling on my face so many times at the first one.
Dan Siroker, Limitless’s co-founder and CEO, also felt a similar weight going into his next startup, mainly because his first company, Optimizely, is still operating and scaling.
“I had a little bit of a chip on my shoulder too. I want this to be the category-defining company that my last company could have been. I know it sounds silly, because Optimizely did do well and is still doing well, but it’s relative to what it could have been. That gap is what gives me energy and fuel and passion for this around,” he says.
“I had some fear going into my second company that it wouldn’t live up to my last one. I had an irrationally high bar even being able to talk about what I was working on that a first-time founder doesn’t have. A first-time founder just wants something to be successful. They almost don’t care what it is. That’s been the biggest psychological challenge this time around.”
When you start from zero, nothing is ever going to be perfect. You need to be willing to embrace that, and not let it get to you. They say perfect is the enemy of good, and I subscribe to that.
In terms of how to weather that failure, Bob Moore points to the importance of self-care strategies. (He’s previously relied on exercise and improv comedy.) “Don’t underplay that aspect, it’s truly a big deal,” he says. “Sometimes the company’s operational failures are actually outputs of the founder succumbing to decision fatigue. Or becoming overly paranoid or personally stressed. Or not having the energy to build the support system that they need to succeed.”
Discover what other lessons in resiliency Moore learned from building three startups here.
Distance can make you a better decision-maker
When Dennis Pilarinos was heads-down working on his first startup, Buddybuild, he was burning the candle at both ends. “Any number of people told me, ‘You’re running a marathon at a sprint pace, you won’t be able to sustain it,’” Pilarinos says. “My internal dialogue was like, watch me.”
His behavior here most likely resonates with any founder. When a big part of your identity becomes tied to your work, it’s only natural to throw every ounce of yourself into your startup. But with the benefit of hindsight, Pilarinos now feels this mentality hurt more than it helped him in the long run.
“Now I have evidence that distance from the problem helps you solve it better,” he says. “When I take a day away from the things I’m mulling over or that I just can’t seem to wrap my brain around, I come back to the problem and it’s simpler to resolve. Without that distance, you start to lose the forest for the trees. It can lead you down a different direction, and sometimes it’s the wrong one.”
When you can see what is a tree from what’s a forest, everything becomes a lot clearer. It’s counter to the feeling of perseverance, where you feel if you keep hacking away at this one thing, you’ll eventually figure it out.
These days, Pilarinos is diligent about time-blocking one day of the week and dedicating it entirely to rest. “I’m very principled around the amount of time that I spend on a weekend working,” he says. “As a first-time founder, it was foreign to me that other people wouldn’t be going into the office on a Saturday, as I had done so for so long. Now I’m particularly strict around my Saturdays. I have a no phone, no computer rule. I actively try to do anything else.”
This simple buffer has helped Pilarinos stay at equilibrium amidst the high highs and the low lows of startup life. “You’re never as bad or as good as you think you are. It’s easy to say, but really hard to internalize. And so on the days that you land that big deal, you’re like, ‘I’m invincible.’ And then when the system is down for an extended period of time or a demo goes poorly or a customer churns out, you think, ‘Well, this is the end of the world,’” he says.
“With Buddybuild, I lived so intensely moment to moment where it was very, very unhealthy. Now it still hurts, but I think I have a little bit more perspective to realize that it could be better, it could be worse — and it will be.”
You can find all of Pilarinos’ essential lessons from building two startups here.
Reshape your quest for fulfillment
Founders spend arguably their most valuable currency, their time, for years on end, with no guarantee they’re ever going to see a return on the investment.
Understandably, this raises a few existential questions about how to keep yourself going, especially when you’re in it again for the long haul. Feeling fulfilled with the job can be a huge internal motivator to keep founders going, but over-index on it, and you are more likely to come up empty. And it’s a lesson that Clay’s co-founder and CEO Kareem Amin learned the hard way.
His first company, Frame, was acquired by Sailthru in 2014. A couple of product leadership stints later (including one as VP of Product at the Wall Street Journal) Amin was itching to get back into entrepreneurship. But this time, he wanted to approach things differently, mainly by being mindful of his mental health.
“A challenge I had the first time around was treating my company too much like my art project,” Amin says. “It ended up decreasing the quality of my decision-making, and it would lead the whole team to spiral. Because I was putting too much pressure on it to be successful and fulfilling,” Amin says. “But that’s tricky, right? Because for something to be fulfilling, you have to both enjoy it, and it has to align with your ideals and goals.”
This quest for fulfillment, in part, came from Amin’s previous experience with clinching a successful exit for his company. He felt the weight of doing it again on his shoulders. “There’s this pressure to make the biggest thing. You keep asking yourself is this the biggest market? But I don’t think that’s actually what’s most valuable,” he says.
“When I started to shift my mindset to say, well, my startup doesn’t have to be the biggest thing. It just has to be what I think is useful and what other people think is useful. And let’s just start there, without putting all that pressure on it needing it to be something other than what it is. So now I approach the problem with curiosity. I ask: well, what does this want to be?”
ON EXPLORING IDEAS AGAIN:
Once you’ve mentally prepared to pick up your tools and start building again, the next step is to start sketching out what shape your product will take. Though typical startup lore has led many to believe inspiration seems to strike at random, repeat founders know that a great idea needs to be validated. And that means doing your homework.
There’s lots to consider in this ideation stage — it’s also the pivotal time to start searching for the right teammates you will bring along for the ride. In this section, we’ll dive into two founders’ examples of the first move they made once they mentally prepped to start building again.
A tangible framework for choosing your next startup idea
After nearly 10 years deeply embedded in the world of product-led growth, Neha Narkhede was ready for a new challenge. However, what exactly she wanted to build wasn’t as clear.
Her first startup Confluent, was an open-source project spun out of the data event streaming platform Apache Kafka that Narkhede co-authored while still an employee at Linkedin — and it eventually went public in 2021. After navigating the thorny complexities of building open-source software and transitioning that to a thriving SaaS business, she was on the hunt for a different type of challenge.
“I wanted to experience building a traditional SaaS company, starting with a closed-source product, working with a few early customers, taking it to market, and slowly starting to build the company,” Narkhede says. “The two worlds are so different that just from a curiosity perspective, I knew it would keep me going as a founder because I would learn something new every day.”
So when the opportunity presented itself to embark on a new venture, Narkhede knew she had to act fast. Intrigued by the risk assessment and fraud space from her previous startup, she went full force on launching Oscilar as a closed-source, B2B SaaS startup.
Pulling from her insights as a previous founder, she was able to expedite the validation process by leaning on these two tactics:
1) Study the market.
- “If you follow the market and there’s a huge transition happening and you are offering the most powerful differentiated product, then that’s the right problem to jump on. That was one of the big reasons why I picked the fraud and risk space — especially with a pandemic, everything was moving online and there still wasn’t a right solution that’s real-time and AI-powered that solves this problem.” As a bonus, she had seen folks at both Confluent and LinkedIn struggling with fraud and risk, so that was an extra dose of confidence that there was a huge market to tap into.
2) Talk to buyers.
- “I set up meetings with 70 or 80 prospective buyers who were heads of risk at different companies in different industry verticals. I literally showed them a Figma prototype if they were to use a product like Oscilar to get that customer research to a point where people were ready to buy something — if only it existed. That was the deeper next step of validating if this was a real problem that people were willing to pay for. That’s the most critical part of customer research that leads to successful companies.”
If your co-founder relationship isn’t broken, don’t fix it
As you start pulling the pieces together for another venture, it is just as wise to consider who you’ll start another company with, as it is to nail down what product idea you will explore. And if the threepeat co-founders of Pilot represent anything, it’s that if you hit a groove with your co-founders the first time, don’t be so quick to toss that aside.
Now on their third startup together, Jessica McKellar, Waseem Daher, and Jeff Arnold have been working in tandem since they met as self-professed computer nerds at MIT. “The nerdiest of the computer nerds hung out at the computer club,” jokes McKellar. “And that’s where we met.”
The first company they built out of college, KSplice, was acquired by Oracle. A year and one day later, the friends were back at it again to start Zulip (acquired by Dropbox). Now they steer the ship at Pilot — a bookkeeping and tax services startup with customers like OpenAI, Lattice and Airtable.
While he was moderately intrigued by the idea of what would become Pilot, that wasn’t the true pull for starting a bookkeeping company, according to Daher. To hear him tell it, he was so determined to work with McKellar and Arnold again that he was willing to do so at the expense of feeling stoked on the idea itself.
Far and away, the number one thing I optimized for my next startup was working with smart, talented people who challenged me to do my best work every day.
McKellar and Arnold were on the same exact page — so the three were very deliberate about only focusing on pursuing startup ideas that the entire founding trio agreed upon. “My co-founders and I started working together because we thought we were the most effective company leaders that we knew,” McKellar says. “And then we stayed together because we proved that we were so effective as a group.”
A smooth co-founder relationship is a rare thing to experience, I would never let go of it. I think that statistically, I wouldn’t find it again, if I were to try to start another company with other people.
For those looking to reverse engineer some of the magic of the Pilot co-founders and weave it into their own, Daher shares the three tactical pointers to optimize for with your founding team:
- 1) Constructive tension. “It’s not always smiles and roses and unicorns or whatever, there’s always tension, but it’s a healthy, constructive tension. In any long-term relationship, whether it’s your close personal friends or your spouse, it’s not like you can never fight, we certainly do, but the undercurrents that have allowed it to work are a strong mutual trust and respect for one another. Jeff, Jessica, and I each have big non-overlapping areas of ownership, and we trust one another to execute well in those areas of ownership. So, there’s very little toe stepping, there’s very little getting up in each other’s businesses.”
- 2) Shared Trust. “We have had a track record of working well together. I know that if Jeff or Jessica says, ‘I’m going to do X, Y, Z,’ I know that they’ll do it, and vice versa. I could tell you, I think with 95% confidence what Jeff or Jessica would do or think in any given situation and vice versa. And the power of that is actually that we know when something is going to be controversial, and when the three of us should discuss it, as opposed to, ‘Oh, this is a thing that is fine if I just go do it.’ If there’s an important thing, the three of us should talk about it. I don’t think that like you’re off building your own fiefdom or you’re going to go do something sneaky that is in your interest and not my interest.”
- 3) More energy in the reserves. “A huge advantage of working with the same people as before is we can focus more of our mental energy on making the company successful, as opposed to spending that time debugging the founder relationship. One of the most common causes of death for a company in the early days is founder drama, so being able to solve for that from the get-go is very valuable in increasing the probability or the likelihood of success of the company.”
Just as the Pilot team optimized for happiness by getting the band back together, Dennis Pilarnos brought several of his former team members at Buddybuild with him for his second venture, Unblocked. “Sharing the same set of beliefs in how we operate was important to us the second time around,” Pilarnos says.
When building with the same folks, he encourages other repeat founders to be mindful of checking their priors and reassessing old processes.
“It’s an interesting dynamic because as we’re growing the team now, we have this pre-baked culture and perspective on things. There were 10 of us that started right out of the gate together where we have that shared that background. So as we bring people in, I’m very mindful and explicit in observing what predispositions we have that we need to reevaluate or reassess. Make sure you can answer: What makes them special?”
ON STAYING SHARP WHILE BUILDING
When you build one company and it’s successful, founders run the risk of hardening their view on the right way to do something — on everything from how to build products to how to distribute pricing and packaging and so on.
But there’s also a hidden variable problem, where often things work in ways that you might not entirely understand. Put simply: did things work because of that thing or in spite of it?
In this section, repeat founders share some of the biggest potholes they’ve driven over and what they think would’ve made for a smoother ride.
Stay in front of customers, always.
When serial entrepreneur Steve Blank was just starting out in his career, he reported to a repeat founder and CEO. “The founder was incredibly successful at his first company. He took it from 0 to $400 million, and this was back in the 1980s,” Blank says. “He was out in front of customers all the time, always listening, always pivoting.”
Fast forward a couple of years, and Blank was working at this founder’s second venture. He noticed something markedly different about where the founder spent his time. “Guess where this CEO was? In front of customers? Hell no. He was wining and dining investors. And who was spending time in front of the customers? I was,” Blank recalls.
“What I found in those customer conversations was that we were building a product no one wanted. When I went back to tell this founder, what do you think was his response? He said, ‘Hey, I raised money based on these promises, go back and try to sell this stuff.’”
If you look at what makes or breaks a second startup, luck has something to do with it, and hubris has a lot to do with it.
These days, Blank teaches entrepreneurship and national security innovation at Stanford. He’s been a part of or co-founded eight different Silicon Valley startups — running the gamut from semiconductors, video games, personal computers, and supercomputers.
But this early experience is one that stuck with him throughout his whole career. “What this founder didn’t realize is it was their customer insight that was the key to his initial success, not his own.”
There’s no guarantee that you are going to learn from your successes or failures, but what I’ve found is this: If you can’t draw it on a whiteboard or you can’t teach it to someone else, you probably haven’t learned anything.
More of Blank’s lessons on mastering entrepreneurship and studying customers here.
Place a focus on focus
Focus is a finicky thing for startup founders. There’s lots of conventional startup wisdom out there pointing to the rewards of staying diligently on task, and other more contrarian takes that pivoting is a healthy (and even necessary) part of the path to product-market fit.
But after experimenting with both of these approaches at his last startup and the beginning years at Clay, Kareem Amin leans toward the former.
“An issue I had is I would get excited about something else in the middle of a sprint and start doing that,” Amin says. “If a customer told us that they needed a certain feature then our product would be great, we’d switch gears entirely. I had to learn to discipline myself and the team.”
To practice more rigorous focus, Amin took a closer look at embedding focus into his day-to-day routine, even taking a magnifying glass to his conversations.
“It took a lot of work to shift my attention and perspective to say, the vision part is not the problem. Our ambition was large. What was missing was clarity around what I was working on each day. And the next day. I started telling people once we agree to something and it’s on our sprint planning, nothing will shift it. If you’re walking to work and you happen to have a new idea, throw it away. You hear a lot of people give the advice to stay focused, but what is focus?” Amin says. “Some folks think it’s dedicating your mornings to some work and then at night you switch gears to something different.”
For me, focus means that I don’t even think about anything else. If you even start the sentence, ‘imagine this other world…’ in your head, you’re not focused.
Play the instrument you’re best at
For most founders, the prospect of relinquishing the CEO role as their company crosses the Series A threshold would be unthinkable. But Lloyd Tabb is not your typical founder. He’s learned through hard-won experience that sometimes the best path forward means making tough decisions and letting go of control.
After fighting in the fundraising trenches with his business partner (and Looker’s President at the time) Frank Bien, Tabb realized that Bien deserved the CEO title. “Looking back now, I firmly believe the reason that Looker has executed to the degree that it has is because we brought in professional management,” says Tabb. “It was obvious that Frank was a man of very high integrity and he knew enterprise software — he knew how to execute in this space. So while it felt like I was taking a risk by turning over the CEO role and committing us to the enterprise route, I reminded myself that startups are all about risks — and he was a much better bet than I was.”
As a repeat founder, I often like to say that I’m a one-man band. I’ve played all the instruments and can do just about every startup job. But that doesn’t mean I do them all well. Keep the instrument you’re best at, and give the rest away.
