How great founders source their purpose and stay motivated through good times and bad

Start with the "why" before the "what" and other essential lessons from the founders of Pinterest, Cameo, Chief, and HealthAllies.

This is Lesson 1 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.

Entrepreneurship is notoriously hard. Most startups fail, and even experienced investors can’t always predict which entrepreneurs and ideas will beat the odds (we have an entire portfolio of missed opportunities to prove it). 

But the successful founders we’ve spoken to for this series had at least one thing in common: tenacity. Today’s lessons are all about finding — and sustaining — your motivation so you can turn a great idea into a great business, and weather all the storms along the way. 

You’ll read four early founder stories, a test to determine if a business idea is the idea, what to watch out for as an “insider” vs. “outsider” founder, and why a little naiveté can be an asset.

1. Start with the “why” before the “how” or “what”

Back in 2010, founder Evan Sharp was moonlighting on a passion project called Pinterest. Since then, design has played an essential role in putting Pinterest into the hands of 300 million users worldwide. 

When Evan interviews a designer, he always asks why they decided to apply to work at Pinterest. ”I’ve found that designers especially want to work on things that are meaningful to them. If a candidate doesn’t love the why, it’s probably best to move on.” 

The same advice applies to founders. The “what” and “how” of your company are your job, but the “why” is your fuel for both. A weak “why” can lead to settling early, burning out, or otherwise falling short of your original vision.

"Most products reach a fraction of their potential because many stop at extrinsic motivators. It’s tempting to stop doing the work when we find something that works. To push past that, you have to be in touch with your intrinsic motivations.”

In our interview, Evan also discusses ruthless prioritization in the early days of Pinterest, the mandate for diverse customer data, and how to know if you’re solving an actual problem. Keep reading

2. Test the strength of your conviction

Cameo founder and CEO Steven Galanis left college having already built a successful company that hosted parties on campus and eventually expanded into DJ rental equipment, t-shirt retail, and even hot dog stands. 

Steven’s passion for entertainment led him to get involved in a few projects in the film and sports industry while still working full-time in sales at LinkedIn. These extracurriculars inspired the idea for Cameo, but Steven feared leaving his stable job to pursue something so uncertain. 

One conversation on a work trip changed everything. His co-worker saw his hesitation and pushed Steven to confront it. “He said, ‘This idea is too big. If you don't do this and somebody else builds this as a billion-dollar company, could you live with yourself?’”

Steven’s answer came to him immediately. “Nobody had asked me that question before, but the answer was so obviously no. For aspiring entrepreneurs out there, if the answer to that question isn’t ‘no,’ then don't do it. It's too hard.”

In our interview, Steven also discusses the dangerous allure of a big market opportunity, the origin story of Cameo, and the highs and lows of building the business in the midst of changing market conditions. Keep reading

3. Commit to the idea you can’t stop thinking about

Carolyn Childers approached the decision to start her own company with caution, despite having already scaled Handy, Quisid, and other businesses that had huge success. “Being a senior executive and being the founder are two very different things. I needed a mission that I could pour myself into.”

Around the same time she began seriously considering entrepreneurship, Carolyn was witnessing the beginnings of the #MeToo movement, and reflecting on, among other things, her own challenges with networking advancement as a woman in the high ranks of leadership. 

“I decided to go on a personal journey to address this gap. I started to look at other businesses that offered professional networks and support, and didn’t find anything that I myself was eager to join,” she says. “So I decided to build it.” 

During the early stages, Carolyn found herself facing skepticism, but she had her own conviction to fall back on. She knew there were other women out there searching for the same kind of resource, and she proved herself right. Today, Chief has more than 20,000 members. 

In our interview, Carolyn also discusses her transition from the Fortune 500 to early-stage startups, why autonomy and trust the best teachers, and how too much money can stifle learning. Keep reading

4. Expect to be underprepared 

Founder, author, podcaster, and public servant Andy Slavitt has clearly had a storied career. But 30 years ago, he was working as a consultant and unsure about his path. All that changed when Andy’s friend Jeff passed away, and he watched as Jeff’s wife dealt with a pile of medical bills on top of her massive grief.

This tragedy led Andy to start HealthAllies, a service to help Americans without insurance get care. “If you'd asked me a year before if I'd ever be an entrepreneur, I’d have said no,” says Andy. “I'm not a natural risk-taker, but the most profound experiences I've had were huge risks.”

Andy’s first year of entrepreneurship was rife with lessons learned the hard way. “There are a lot of things that it's good that I didn't know. Because I don't think you can do it with full knowledge. I think there’s a certain amount of naiveté that allows you to go for it.” 

One of Andy’s biggest initial shocks was learning “if you build it they will come” is a total myth. “I remember the moment we turned on the website. We just assumed that we were gonna get flooded…and crickets” But by then, Andy was far too determined to turn back. He forged ahead.

In our interview, Andy also discusses getting a crash course in crisis management at a national scale and the importance of staying close to those most impacted by the problem you’re solving. Keep reading

5. Know your relationship to the problem — and its pitfalls

As reflected by some of the stories we’ve shared already, the instinct of many founders is to address a problem they’ve experienced personally. Bessemer Partner Adam Fisher refers to these founders as the “insider” archetype. 

“As an insider, you are approaching the problem as a confident expert, which can give you a powerful edge when pitching investors,” says Adam. “Insider founders can also speak to prospective customers as peers, which lends immediate credibility.”

But being an insider founder comes with its fair share of disadvantages too. Namely that “you’re less likely to think ‘out of the box’ and challenge prevailing assumptions in both the product and go-to-market strategies.”

Unlike insider founders, “outsiders” don’t have conventional wisdom to fall back on, and in some ways, that can actually benefit their companies. “Since outsiders don’t know the proverbial rules of the game, they tend to approach product and GTM in ways that insiders either wouldn’t consider or wouldn’t dare.”

But this naivete can be a liability as well as an asset. As an outsider, it’s easier to underestimate the competition, product complexity, or difficulties acquiring customers  “Hubris and impatience have doomed many outsider founders given what is often a long and expensive learning curve.”

According to Adam, much more important than your relationship to the problem is recognizing how that relationship can influence your perspective and approach. “The power comes from the self-awareness of the archetype and how that can inform future decisions.”

In this guide, Adam Fisher gives aspiring founders four stimulating questions that can help them overcome mental blocks and hang-ups as they decide on a new idea for a startup. Keep reading

Bonus exercise

Read Adam Fisher’s four-part brainstorming framework for founders, and then complete the following exercise. 

For aspiring founders

  1. Answer Adam’s questions below for a startup idea you’re considering.
    1. Do you seek to solve a problem you know well as an “insider” or solve someone else's problem as an “outsider”? 
    2. Do you innovate in an existing product category or attempt to create a novel product category?
    3. Do you favor a widely applicable product with a large market, or focus your product on a smaller, well-defined customer segment?
    4. Do you jump on the bandwagon of a “hot trend” that has investor attention or pursue something under the radar and longer-term?
  2. Write down any new pros/cons or iterations inspired by what you read.
  3. Repeat step #1 for any additional ideas. 

For current founders

  1. What founder archetype do you fit into?
    1. Insider
    2. Outsider
    3. Outsider with a network of insiders
  2. Now, think of a decision you’re pondering or a problem you need to solve.
    1. How do you think your archetype influences your thinking?  
    2. How might a founder with another archetype approach it differently?
    3. Are there any lessons from that approach you can incorporate into your own?

This is Lesson 1 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.