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The Uncomfortable Truth: A 3X Founder's Guide to Intellectual Honesty
Founders are born optimists. It’s basically a job requirement—you have to suspend disbelief to build the future you imagine.
But unchecked optimism has a dark side. When you’ve risked everything for your startup, “happy ears syndrome” can sneak in: subconsciously filtering out anything that challenges your narrative.
Bob Moore, a three-time founder, hit this wall with his first two startups. Both were solid—but not spectacular. Looking back, it was easy to blame timing, market forces, or competition. What he now emphasizes is the role of his own judgment as a young founder.
Moore’s first company, RJMetrics, launched post-2008 downturn. He and his co-founder survived a rough bootstrapped start, found product-market fit, but ultimately got outpaced by competitors. RJMetrics was acquired in 2016, but Looker’s $2.6B exit to Google stole the spotlight. His second startup, Stitch, sold faster, but still fell short of the IPO-level success he aimed for.
“If I had to distill one lesson from back then—and something I’ve obsessed over since—it’s intellectual honesty. Every founder should care about it deeply,” says Moore. Intellectual honesty is the willingness to seek the truth even when it proves you wrong.
For founders, this means separating noise from signal and confronting what isn’t working. In this interview, Moore turns intellectual honesty into actionable strategies, illustrating them with his experiences at RJMetrics, Stitch, and now Crossbeam (a “LinkedIn for data” partnerships platform).
Find a Co-Founder Who Balances Your Thinking
One of the earliest, most consequential choices for a founder is picking a co-founder. Moore emphasizes adding intellectual accountability to your criteria.
He credits his co-founder, Jake Stein, for teaching him critical lessons in intellectual honesty. Early on at RJMetrics, Moore would bring ideas from the latest “hot startup book.” Jake’s response: “Cool, but what didn’t you agree with?”
“I’d never been pushed to hold two conflicting thoughts at once—that a book could be brilliant and flawed simultaneously,” Moore recalls. Over a decade of partnership, they refined this skill, a cornerstone of intellectual honesty.
“Jake was the Charlie Munger to my Warren Buffett. Over time, we both learned to hold two opposing ideas at once without defaulting to blind optimism,” Moore says.
Get Honest About Founder-Market Fit
After selling Stitch, Moore wanted his next venture to be bigger. He dug up a running list of 100 startup ideas—everything from B2B SaaS tools to escape room franchises.
The bias: Over-falling for the problem itself. Many founders “fall in love with the problem” but overlook their own strengths, chasing market trends or personal passions instead.
Moore admits RJMetrics suffered from this. Fresh from VC, they entered the analytics space without a strategic angle—relying on hustling and customer feedback rather than long-term vision. The result: product decisions by committee, leaving growth capped.
The solve: Map ideas on a 2x2 matrix—interest vs. ability.
- Intellectual interest: Will I enjoy building this?
- Founder aptitude: Does my experience give me a unique advantage here?
This exercise shrank Moore’s list from 100 ideas to 10–15 viable options. Past ventures’ positions on this matrix explained why they were “base hits” rather than IPO-scale.
Seek Feedback from Fellow Founders
Moore skipped the traditional customer validation and pitched top ideas to experienced founders instead. Founders offer high-level perspective and can spot risks or opportunities that customers might miss.
The bias: Founder Midas touch. Optimistic founders can inflate the perceived potential of an idea. Friends may also avoid candid criticism.
The solve: The forcing function of choice. Moore asked founders to rank their three ideas. By making them compare and justify, he got honest feedback.
Crossbeam quickly emerged as a winner. Early conversations revealed a natural viral loop—founders were already pointing Moore toward potential customers.
Discern True Product-Market Fit (and Watch for Warning Signs)
RJMetrics initially showed traction but lost momentum as competitors like Amazon Redshift, Tableau, and Looker shifted the market. Moore identifies biases that blinded him:
- “We know better than they do” mentality: He rationalized churn as customer error and dismissed competition.
- Selling to your network: Early revenue doesn’t always reflect real demand; friends may pay just to avoid awkward conversations.
The solve: Pay attention to dismissiveness and social capital. True PMF emerges when people spend their own credibility or resources to use and promote your product. Crossbeam’s network-driven model forced this reality check.
Growth-Stage Test of Intellectual Honesty: Merging with a Competitor
Founders often resist joining forces with competitors. Moore did it anyway with Reveal, after customer demand made collaboration unavoidable.
The merger wasn’t about ego—it was about scale and customer impact. Moore emphasizes that intellectual honesty sometimes means letting go of pride to maximize long-term value.
“What mattered was building the biggest, most impactful company possible—not whose logo was on the business card,” Moore says.
