From Yext to Roam: Howard Lerman’s Second Act
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this compelling episode of Grit, Kleiner Perkins partner Joubin Mirzadegan sits down with Howard Lerman, founder and CEO of Roam and former CEO of Yext. (00:00) Howard shares his highly regimented daily routine that has enabled him to build billion-dollar companies while maintaining peak physical and mental performance. From his meticulously scheduled workouts to his philosophy on founder friendships, Howard offers a raw, unfiltered look at what it takes to succeed as a serial entrepreneur. (14:00) The conversation explores how Howard's approach to company building has evolved from his first startup at age 19 through taking Yext public and now building Roam into what he believes will be his biggest company yet.
- Core themes include the intersection of personal optimization and company building, the sacrifices required for entrepreneurial success, and the evolution from building for Wall Street to building authentic solutions
Speakers
Howard Lerman
Howard Lerman is the founder and CEO of Roam, a virtual office platform where humans and AI work side by side from anywhere. Previously, he co-founded and served as CEO of Yext for 15.5 years, taking the company public in 2017 and scaling it to nearly half a billion in recurring revenue before stepping down after 22 quarters as a public company CEO. Howard began his entrepreneurial journey at age 19 with his first company "Just A Tip," which went viral after being featured on The Daily Show, and has been building companies for over two decades.
Joubin Mirzadegan
Joubin Mirzadegan is a partner at Kleiner Perkins and host of the Grit podcast. He focuses on exploring the personal and professional challenges of building history-making companies, having conducted over 260 episodes with successful founders and executives. Before joining venture capital, Joubin had operating experience and brings a unique perspective on the intersection of company building and personal optimization.
Key Takeaways
Radical Routine Optimization Enables Peak Performance
Howard follows an extreme daily routine that eliminates decision fatigue and maximizes productivity. (04:00) He wears 50 identical shirts, has 8 pairs of the exact same shoes (coded for rotation), and follows a strict schedule including morning reading, dual workouts, and intermittent fasting. This systematic approach isn't about discipline for discipline's sake - it's about freeing mental energy for what matters most. When every micro-decision is automated, founders can dedicate their full cognitive capacity to solving complex business problems and making strategic decisions.
Friendship Is a Luxury Founders Can't Afford
Howard candidly admits he has "cut friends" to focus on building companies, explaining that founders face so many demands they simply don't have time for traditional social activities. (16:40) However, he reframes this sacrifice by noting that the deep bonds formed with co-workers during the intense process of building a company together provide the same social connection and emotional support that friendships normally would. The relationships forged "in the trenches" of entrepreneurship create deeper connections than casual social friendships.
Solve Problems You Experience Personally
Howard emphasizes that successful companies emerge from bottom-up problem identification rather than top-down market analysis. (34:00) He advocates for solving problems you personally feel rather than trying to identify markets to serve. When you build for yourself first, you're guaranteed to have at least one satisfied customer and genuine product-market fit. This approach grounds companies in real pain points rather than theoretical market opportunities, leading to more authentic and sustainable solutions.
Money Provides Freedom to Speak Authentically
Financial success from Yext gave Howard the freedom to "say whatever the f*ck I want," marking a shift from trying to please Wall Street to building authentically. (48:08) He contrasts his experience running a public company, where legal constraints limited authentic communication, with his current approach of building and communicating without filtering his personality. This authenticity extends to product development - rather than building what analysts want, he's focused on creating solutions that genuinely serve users' needs.
Growing Up Together Creates Unbreakable Partnerships
Howard met his wife at age 20 and has worked with many of his core team members for over a decade, with some relationships spanning 31 years back to middle school. (40:00) This longevity creates partnerships that can weather the extreme demands of entrepreneurship because both personal and professional relationships evolved together. Rather than trying to change established relationships to accommodate an entrepreneurial lifestyle, growing together allows for mutual adaptation and deep understanding of each other's needs and boundaries.
Statistics & Facts
- Howard maintains 12% body fat and aims for under 10% for his birthday each year, weighing himself daily with a target of under 175 pounds at 6'1". (04:48)
- Roam has reached $2.5 million in ARR with only 27 employees, 24 of whom are in design and engineering, with no dedicated sales staff. (65:54)
- Howard worked with his core team members for an average tenure of more than a decade, with some relationships spanning 31 years back to middle school. (76:03)
