Five founder lessons on building resilience and bouncing back from rejection

When you're going through hell, keep going and more courageous advice from Okta, Rocket Lab, Stanford, PagerDuty, and UiPath

This is Lesson 5 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.

It’s common for success stories to leave out or gloss over failure, rejection, and losses in service of telling a simpler story. But in nearly every case, such experiences are part and parcel of doing anything difficult or truly novel. 

In the case of entrepreneurship, what often separates achievers from the “almosts” is not just experience and skill, but also persistence in the face of setbacks, and the willingness to give an unlikely goal one more good honest try. 

A Harvard Business Review study backs this up, finding startup teams that reported high levels of previous experience but average to low levels of passion and vision were overall weaker compared to groups of teams with lower levels of experience but higher levels of passion of vision. 

Leaders from UiPath, Okta, PagerDuty, and Rocket Lab share lessons learned on their own winding roads to success. Plus, you’ll get an (optional) assignment from a Stanford professor who believes there’s a lot we stand to gain by focusing on our failures.

1. Treat pivots as training for leadership

After a brief stint working at Microsoft in Seattle, Daniel Dines returned to his home country of Romania to start what would eventually become UiPath, a business now valued at $10 billion. Like most “overnight successes,” Daniel took many years — and a few major pivots — to ultimately triumph. 

Daniel’s first entrepreneurial venture was an outsourcing services company. It took eight years to grow from zero to $500K in annual recurring revenue (ARR), after which Daneil decided to make a short-lived foray into consumer products. Daniel sums up the experience like this: “They didn't work.” 

So Daniel pivoted once again, this time into an original equipment manufacturer (OEM) business. It achieved only a modicum of success, but a few years in, Daniel and his team realized they had an opportunity to productize the services they offered. With that decision, the business took off.

It was only with the benefit of hindsight that Daniel was able to recognize all these early missteps and failed attempts as the boot camp he needed to eventually earn the CEO title and lead UiPath to major success. “My winding path was essential for my formation as CEO.”

In our interview, Daniel also discusses re-making the same decision (over and over), building an international GTM strategy early, and remaining calm in the face of competition. Keep reading

2. When you're going through hell, keep going

At Salesforce in the early 2000s, Todd McKinnon became convinced there would soon be a cloud version of every tool in a company’s tech stack. Most investors didn’t have Todd’s foresight, so, while raising for the startup that eventually became Okta, he was met with significant skepticism.

The need for an identity management solution for the cloud didn’t register, no matter how Todd and his co-founder framed it. “Being innovative is by definition lonely. Everyone is questioning if it’s going to work.” But instead of turning others’ doubt inward, the pair maintained conviction. 

It paid off. A few years into their journey, a miraculous thing happened. Microsoft started selling Microsoft 365, its cloud-based suite of work tools, a major product that — you guessed it! —- necessitated an identity management solution for the cloud. Microsoft launched its own. 

Microsoft’s competitive product validated the market for Okta overnight. The experience made Todd steadfast in his message to dejected founders trying to build something novel. “You’ll go from a lonely category creator to owning the whole thing. All that pain is paid off — you’re the de facto leader. And all that marketing you were doing that people thought was bad? Suddenly, it works.”

In our interview, Todd also discusses the very early days of Okta, how he learned to differentiate between advice to follow and advice to ignore, and the obligation of entrepreneurs to give back. Keep reading → 

3. Don’t discount your informal experience

Rocket Lab CEO Peter Beck’s earliest memory was staring up at the night sky with his father. “He pointed out all the stars and told me that every one of those stars has a planet, and there could be somebody on a planet looking back at me. That got me interested in space.”

Today, Rocket Lab touts the highest launch success rate of any rocket company in history. The team builds launch vehicles, communications constellations, and spacecraft for interplanetary missions. So far, they’ve launched 160+ satellites and sent their technology to the moon.

There’s a lot that’s unconventional about these accomplishments, including Peter’s lack of formal education in rocket science. Beginning in childhood, Peter was pursuing the studies himself, whether that was attending meetings with academics or building rocket bikes (much to his parents' chagrin).

Later, when he attended a university that didn’t have a rocket science program, he read books, corresponded with experts in the U.S, and built and tested his own designs. “I would run two shifts in my life. I had the day shift where I created the financial resources to do the night shift — building rockets.”

Peter’s lack of formal experience ultimately gave the RocketLab team an innovative edge. “Nobody we hired had any space background. That was part of the magic. Going from first principles and the latest technologies, we were asking, ‘What’s the best way to solve this?’” 

In our interview, Peter also discusses other memorable moments and lessons learned on his unlikely, passion-fueled path to building a billion-dollar rocket company. Keep reading → 

4. Never miss an opportunity to learn

Jennifer Tejada was deeply affected the first time she saw code as a young girl. “I was struck by the realization that you could turn nothing into something. You could literally make a rocket launch with a series of zeroes and ones.” Her early fascination led her to pursue a career in the tech industry, where she ultimately became the CEO of PagerDuty and led it to an IPO in 2019.

Like many in her shoes, Jennifer’s huge success story belies all the difficult moments she faced along the way. Jennifer remembers the worst one in vivid detail. While she was 30,000 feet in the air, a distributed denial-of-service (DDoS) security attack shut down half the internet, putting PagerDuty at risk because of its dependency on cloud providers and services. 

“When trust and reliability is literally your number one value proposition to customers, this situation is a nightmare. I was so worried I’d let people down.” Luckily, Jennifer and her team resolved the incident with only a short period of website downtime and minor website delays. 

After this incident, Jennifer and her team extracted significant learnings that they were able to apply to protect the business against future threat. She now attributes much of PagerDuty’s resilience during the pandemic to these learnings 

“It’s easy to skip extracting wisdom from stressful times after they’re over. You just want to move on. But trust me, your future self will be so glad you did it.”

In our interview, Jennifer also discusses how customer love can help you sidestep gatekeepers in the sales process and why it’s important to periodically reassess your executive team. Keep reading →  

5. Create a failure resume

Dr. Tina Seelig’s diverse career highlights include getting a PhD in neuroscience, starting multiple companies, writing 17 best-selling books, and becoming a professor at Stanford. Despite her many successes, Tina spends much more time reflecting on the failures. 

At Stanford, Tina asks her classes to do the same. Among students, she’s known for her failure resume assignment, in which students are asked to list out academic, professional, and personal endeavors that didn’t go according to plan — an exercise Tina completed herself in in her book, What I Wish I Knew When I Was 20). 

The failure resume has two goals. The first is to take time to reflect on each failure, and mine the experience for insights that can lead to better decision-making in the future. (At Bessmer, we keep an anti-portfolio of great investment opportunities we missed for the very same reason). 

The other goal is to help students let go of judgment and fear that could hold them back. “I don't know why we look at the failures of adults with such disdain when they're doing complicated things that no one has done. It is an essential part of eventually achieving success.”

In our interview, Tina also discusses why it’s worth it to take a too-junior role to get a foot in the door at your dream employer, and what founders risk when they make goals too attainable. Keep reading

Bonus exercise

Create your own failure resume using Dr. Tina Seelig’s framework from lesson one. Make sure to reference key learnings from each failure, including what you’d do differently next time, how it changed you, and how you bounced back. 

This is Lesson 5 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.