10 patterns I found when I interviewed 12 successful founders

I interviewed 12 of the most successful founders out there for Founder Thunder Round, and noticed a few patterns emerge.

I don’t intend to push these as dogmatic truths, but rather simply as observations. Learn from these patterns what you will!

#1: Doing small before you do big

Almost every founder, at some point in the interview, referenced small tests before big bets. After great successes with StartupVitamins, Davis Siksnans and his team sent a webpage about Printful out to their email list before it even actually existed. Tons of people signed up, so they went for it.

John O’Nolan wrote a blog post about his idea for how he would build a modern, open source blogging system meant strictly for blogging. It blew up on Hacker News, he got to work on what became a huge Kickstarter campaign, and a product now even seen on HBO’s Silicon Valley.

Wade Foster manually created the integration that Andrew Warner (Mixergy) was looking for before Zapier had many integrations. And that was only after testing out the idea at a Startup Weekend (taking home first place).

Laura Roeder spent years as a consultant helping businesses use her effective system for running an engaging presence on social media. Realizing demand far outpaced what she could scale to as a consultant, she created MeetEdgar — an app that lets people leverage Laura’s process on their own.

Matthew Bellows says, “it’s a worthwhile process as a founder to set near-term goals. Discrete and clear sign posts to figure out, ‘is this working or not?’” In his case, he decided “if we can’t get our first playing customer [in] four months, I have to do something else.” Sure enough, they did, and Yesware has only grown since.

Sid Sijbrandij submitted just a landing page for his idea for GitLab to HackerNews. After a disappointing start, it ended up trending on the front page, and he knew there was something there. In fact — the entire workflow baked into GitLab is meant to help others reduce the cycle time from idea to production, something they adhere to internally as well.

Sid says that if you have a small change, “it’s very likely to be right, good, pleasing the customer, less risk, and deployed more quickly.” Since it has all these advantages, they try to help people move toward small changes, because they’re much more likely to be good and right. That’s why they baked this thinking into their product with a cycle time tracker.

Dave Nevogt says they make no big bets at Hubstaff — they will throw a lot of small tests at the wall and see what sticks.

I could go on and on. This topic kept coming up. The result is this: small tests before big bets.

Also, the very first FTR episode (click here) gives you an even better taste of how founders knew they should put the pedal to the metal.

#2: Scratching your own itch

Almost every one of the founders was scratching their own itch, or dogfooding, with their product or startup.

At StartupVitamins, they needed a way to print their products on demand. So Printful was born. MeetEdgar was the app-ified version of the consulting service Laura provided her clients, which involved a lot of manual labor. Ghost was John O’Nolan’s dream version of what Wordpress would look like if it was just a blogging platform, and not a full CMS powering a huge percentage of the web. Olark came out of a consulting company that created a live chat to up their support game. Balsamiq wouldn’t exist if it weren’t for Peldi Guillizzoni’s need for a faster and better way to quickly sketch out ideas on the computer.

When people want to start their own company, but say they don’t have any ideas, I always ask them: what problems do you have? What problems do your peers have? Can you solve those? After all, you’re far better equipped to solve the problems you experience yourself.

#3: Hiring the best people

Again, almost everyone harped on this one, a lot. It’s all about the people, these founders say.

Wade told me that during the Y Combinator founder dinners, his mentors constantly told him this. “Hire the best people,” “It’s all about the people.” He says he really didn’t pay too much attention to this persistent advice because they had seemingly much larger fish to fry at the time to get Zapier off the ground.

But now — 5 years in — he says these mentors were dead right. It’s all about the people, he will now also tell you.

The best people may be some percentage more expensive, but deliver 10x the value to your startup, according to these founders.

Wade’s advice: get really good at finding and recruiting awesome people. They make all the difference in the world.

Davis’ advice he would give to 5-years-ago Davis? Pay more attention to hiring, getting the right people on board, and to culture. Same thing for Peldi, who would have told himself to be more careful hiring at the beginning.

Matthieu Vaxelaire, founder of Mention, when asked about his personal definition of success, said that beyond a successful business, “I need to be super excited and willing to fight for my business to be happy and successful.” I asked how he achieves that. His answer: “What excites me most when I wake up and join my team is to work with so many talented people. It drives me insane to see the talent we have here at Mention. This is super exciting,” adding, “hiring very talented people that share the same vision and passion is key to make it a journey you want to be part of.”

He says that it takes a lot of time to find the right people for various skills, but even more for passion-fit, which he says is critical — they have turned down otherwise fully qualified candidates because of a lack of “alignment.”

In fact, many of these founders’ startups are fully remote — allowing them to hire the best people in the world, not just the best in their own backyards.

Ben says that the thing he most overthought was their first fire. It was the right path forward for the company and the employee.

Also, while we’re on the topic of growing teams: when asked what advice he’d give a 5-years-younger version of himself, Ben said he’d hire an executive coach. He said many founders lack management expertise, and this really helps refine that skillset. I can vouch for the same — I hired one years later than I should have at Mindsense, and it makes such a huge difference.

#4: Not their first at-bat

Almost all of these founders have worked on other ideas / startups before, but this is the one that really took off. Davis said this was really helpful because he already knew how to do some things better, like customer interviews and marketing. His prior startup experience meant he wasn’t learning on the job as much as a first-timer would be. (That said, founders are always learning on the job! See #8 below.)

Wade says that he had tried other ideas before, but he knew from the start, this one — Zapier — was different. The wins didn’t come nearly as easily with his previous startup ideas.

The key takeaway here is this: start stuff. Even if you’re still a student. Especially if you’re still a student. Even if the idea sucks. Get to know how to do this stuff: vet ideas with customers, design a product, design a business, market to specific audiences, etc. Even if your first at-bat goes nowhere, it’ll prepare you for when you land on a winner.

Further, many of these founders knew better what they wanted to work on, and how they wanted their own company run, based on what they didn’t like in their prior jobs and startups. Laura didn’t like the business model of shipping books; she liked the much more sustainable business model of SaaS, because it’s better for the customer and the company. A few of the founders knew they wanted to be founders because they really did not like being chained to someone else’s desk from 9 to 5 working on something they didn’t believe in — defining their future companies as fully remote, and results-oriented. Wade says, “I was tired of working at jobs that didn’t share my values.” Success to him? “I want to work in a project the way I think it can be done… I wanted to do what I knew was good work.” He also hated commuting. Not unrelated, besides being all-remote, Zapier offers delocation packages to employees in the valley.

#5: Bootstrapped and self-funded to start

Similarly, many of these founders used money from past ideas to (sometimes significantly) self-fund their new idea. Along with their co-founders, these founders invested $10k, $30k, sometimes over $50k of their own money to get the startup off the ground. Other founders funded their startup with an existing consultancy or other prior business’ existing revenue stream — working on the new idea part-time until its revenues surpassed that of its funder.

Some of these founders have gone on to raise traditional money — one with hundreds of thousands in VC money — but quite a few have intentionally stayed bootstrapped. It’s a lifestyle choice for these founders and their teams, it seems.

#6: No silver bullets

Here’s a theme that you can’t get away from talking to these ten founders: there are no silver bullets.

Wade says, “Often people will say ‘was there an inflection point in the business?’ For us it was just showing up day after day for 5 plus years…and that effort has always led to [getting] a little bit better… You realize if you do that for five plus years, you can actually build something pretty impressive.”

John says, “There are no silver bullets… and I’ve tried them all!”

Laura shares that they’ve always had extremely even growth (and they hit $1m in ARR in under a year!). “Lots of startups have this fantasy of a single moment that will cause everything to take off… You don’t need one of these moments that changes everything. Steady growth is how we’ve gotten there.”

She adds, “A lot of people think, ‘oh we’re going to be on Product Hunt and we’re going to have a business after that.’ We were on Product Hunt, we were on page one. It’s great traffic for one day, then nothing.”

Her advice? “People get really focused on looking for these one-off opportunities like Product Hunt, and it’s much more important to build a long-term marketing machine, which is doing things like blogging, opportunities to get linked in different places, build up a search profile. Marketing needs to be a long-term plan, not just jumping around looking for different opportunities.” Of course, this mentality is baked right into her product, MeetEdgar, which helps her customers build a long-term marketing machine on social.

All of the founders harped on this: there was no major event that caused their revenue to dramatically increase overnight. All of their revenue graphs look pretty much the same: steady increase over five years. All of them steadily crossed $1m ARR at some point, and have kept growing each month.

#7: Exercise

I was surprised by this pattern that emerged among virtually all of these 10 founders, but it makes a lot of sense, given the amount of stress and pressure founders take on — especially as they start to lead larger and larger teams.

They all found something they love: for some it was golf (Dave), others it was racketball (Wade), others it was rock climbing (Ben), others it was biking (Laura), and others, hot yoga (Peldi). But they all stay active.

Matthew says, “Nothing makes me feel more effective than exercising and meditating.”

#8: Life-long learner

These founders are addicted to learning; they find learning new things and approaching new challenges to be engaging work, even if it the work to meet the challenge is wildly un-engaging. What motivates them is learning, and seeing if they can do something new. Because of this, as long as they are in an ever-changing landscape, they will always have the intrinsic motivation they need (as long as things are growing; conversely if things are not growing they would likely become frustrated and bored).

Peldi says that personal success to him is continuing to not know what he’s doing for as long as possible — that’s when he’s happiest. “My best trait is that I can make myself like any job that’s required,” he says, since he takes it as a learning opportunity.

I never really considered this before, but having this trait or mindset is a massive advantage to a founder. Every week presents new challenges to a founder — even years in.

Being addicted to learning and solving ever-changing problems can keep a founder motivated by the nature of their work, rather than burdened by it.

#9: Passion

These founders are all passionate about the content of the work. Matthew Bellows of Yesware — “Email for Salespeople” — has always been passionate about sales. Laura says she always wanted to shift into this SaaS business, but was too afraid for some time.

It seems obvious, as pushing through the despair that often shows up when starting a new company requires a lot more than just a desire to grow a company. The content of the work is meaningful to all 10 of these founders. None of them are entrepreneurs first — they’re something else first, entrepreneurs second.

#10: B2B SaaS

I don’t think there’s a lesson here — but I certainly thought it was interesting that, by chance, when I looked for companies with certain parameters: successful, over 5 years old, have seen the ups & downs, the 12 that got back to me all happened to be B2B SaaS.

You could argue that B2C is a harder business to make sustainable — I know I certainly would. You could also argue that B2C SaaS specifically is near impossible in most categories.

Of course, take this all with a grain of salt — I have a sample size of 12, and a lot of variables that made it non-random.

Bonus: Basic on Productivity

Many of these founders, when asked about their methods to stay productive, explained that they’ve certainly tried a few things, but that their tried-and-true method is: nothing special. They don’t use any special apps or methods, they just know what to do, and then do it.

In fact, some of them reacted with mild disgust when I asked them what tools or methods they use. The answer was easy for them: figure out what to do, and just do it.

John says it best: “Write all the shit you want to get done, got off Twitter, and do the things you want to do. Then repeat that over and over again. Sounds simplistic, but it is that simple. It’s just finding the motivation to stay that focused.”

Matthieu’s succinct advice: “read less, do more.” Here’s what he had to say:

Want more from these 12 founders? Catch the whole series at FTR.rocks, and be sure to subscribe there for new episodes as they drop.




Recommended from Medium

Max Perilstein Of Sole Source Consultants: Five Things You Need To Build A Trusted And Beloved…

Small Checks, Big Introductions

7 Essentials for a Business professional at Impact

Joaquim Miro of GDA Capital: Five Strategies I Used To Grow My Business To Reach Seven Figures In…

Built for advisors: a better way to track your clients’ money


An action-packed July! Alumni Week recap and MORE

Achieving Startup Company Value Innovation

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Alexander Obenauer

Alexander Obenauer


More from Medium

Are you embarrassed by the first version of your product?

Why Venture Building is the Future of How Startups Are Created

Here’s how your startup can raise millions in funding and still fail.