Boardroom Blitz

The Team You Build Is the Company You Build: Scott Holloway on Scaling, Culture, and Leadership

Guest: Scott Holloway, General Partner at Starting Line

What does it take to build a company that grows at breakneck speed without watching its culture, standards, and sanity fall apart?

Scott Holloway has lived that challenge firsthand. As Instacart's 10th employee, he helped expand the company into dozens of markets. He subsequently led hundreds of employees across Flexport's Chicago and Dallas operations before transitioning into venture capital as a General Partner at Starting Line.

In this episode of Boardroom Blitz, Scott joins hosts Jeremie Bacon and Garry Cooper to unpack the messy realities of scaling organizations, hiring exceptional people, and leading through relentless change.

From navigating the operational whiplash of COVID-era supply chains to helping define Instacart's company values, Scott shares hard-earned lessons about what separates great teams from merely good ones.

What we cover:

• The leadership scaling problem: Why leading 20 people is fundamentally different from leading 200, and how executives must evolve alongside their organizations.
• Hiring as a competitive advantage: Why the best leaders recognize their own weaknesses, hire people who outperform them, and raise the talent bar with every new addition.
• Culture isn't a corporate poster: How Instacart developed its values, why founders' personalities permeate their organizations, and what happens when success breeds complacency.
• Demanding AND supportive: Why great companies resemble high-performing sports teams rather than families, and how leaders can combine accountability with genuine compassion.
• Managing through chaos: What Scott learned from rapidly changing hiring mandates, financial pressures, and pandemic-era uncertainty at Flexport.
• What investors actually look for: Founders with conviction, humility, tenacity, and an almost unreasonable determination to bring their visions to life.
• The case for taking bigger risks: Why Scott encourages aspiring entrepreneurs to start earlier, embrace uncertainty, and stop worrying so much about what everyone else thinks.

"The team you build is the company you build."

Scott argues that hiring is perhaps an executive's most important responsibility. Exceptional people don't just do better work. They elevate everyone around them.

He also challenges the idea that organizational culture is primarily about making people comfortable. Great cultures demand excellence while giving people the support, trust, and resources they need to deliver it.

And when it comes to investing, Scott pays particular attention to the speed at which founders learn, iterate, and execute. Great ideas matter, but the ability to turn them into reality matters even more.

Great leadership isn't about having all the answers. It's about assembling exceptional people, setting uncompromising standards, adapting as circumstances change, and staying optimistic enough to keep everyone moving forward.

Oh, and Scott offers one reassuring observation for anyone suffering from imposter syndrome: even people in the biggest boardrooms often make things up as they go.

Join us for a candid, funny, and practical conversation about what it actually takes to build and lead a great company.

*Boardroom Blitz is hosted by Jeremie Bacon and Garry Cooper, produced by Alex Bacon, and presented by 1871

What does it actually take to build and scale a great marketplace business?

Elan Mosbacher has spent much of his career finding out.

Before becoming co-founder and CEO of Pinch, Elan helped scale SpotHero from an early Chicago startup into a national marketplace, working across marketing, product strategy, partnerships, and company strategy. Along the way, he learned that successful marketplaces rarely win by trying to be everything to everyone from day one.

In this episode of Boardroom Blitz, Elan joins Jeremie Bacon and Garry Cooper to unpack his four stages of marketplace success.

Elan explains why founders often get into trouble by jumping to stage four before they have truly earned stages one through three, and why being dismissed as “too niche” can sometimes be evidence that you're doing exactly the right thing.

The conversation also covers the customer research that changed SpotHero's growth strategy, how to challenge founders and executives without turning disagreement into politics, and the lessons Elan carried from SpotHero into building Pinch, a technology-enabled healthcare marketplace operating across multiple states.

The guys also dig into the increasingly blurry line between technology companies and traditional businesses, how Pinch uses AI and software to scale a highly human healthcare experience, and why AI may dramatically change the amount of infrastructure required to build the next generation of growth companies.

Plus: raising kids while building startups, surviving startup “whitewater,” why keeping the wrong employee too long almost never ends well, and the business book Elan thinks more founders should read.

If you're building a marketplace, scaling a growth company, or trying to figure out when to stay focused versus when you've earned the right to expand, this episode is for you.

In this engaging conversation, Garry and Jeremie welcome Josh Linkner, a multifaceted talent who embodies the spirit of improvisation both on stage and in the boardroom. Josh’s journey from jazz guitarist to successful entrepreneur, author, and venture capitalist offers rich insights into the intersection of creativity and business.

As Josh shares his background, it becomes clear that his music career laid a solid foundation for his entrepreneurial endeavors. He explains, “The skills in jazz are exactly translatable to the world of business today.” This connection between jazz and business is a recurring theme, emphasizing the need for improvisation and adaptability in today’s fast-paced environment. 

Josh compares traditional business structures to classical music, where precision and adherence to notes reign supreme. He argues that today’s leaders must embrace a jazz-like approach, thriving in uncertainty and using situational awareness to navigate challenges. **“We have to perform at our best without all the notes in front of us.”** This philosophy encourages creativity and quick adaptation, essential traits for modern entrepreneurs.

The discussion takes a personal turn as Jeremie reflects on witnessing Josh’s passion while performing. He notes, “You can see the joy in your face when you’re playing.” This joy, a hallmark of both musicianship and entrepreneurial spirit, underscores the importance of passion in achieving success.

Josh’s insights remind us that whether we’re on stage or in business, the ability to improvise, listen, and adapt can lead us to greater heights. “We’re being called to lead in a really different way.”

Check out the full episode!

Discover how farm life shaped the journey of G2's co-founder.

Growing up on a farm in central Iowa, Tim Handorf learned invaluable lessons about entrepreneurship before he even knew what that meant. In a recent episode of Boardroom Blitz, he shared insights from his upbringing that shaped his approach to business today.

Farming as a Foundation

Tim vividly recalls the hard work of farm life, saying, "When you're growing up in it, you don't like it, right? It's a lot of hard work. No one likes getting up at 6 AM and shoveling pig crap." Yet, he recognizes that those early mornings and laborious tasks fostered a strong work ethic and resilience.

He reflects, "Farmers are entrepreneurs. I grew up in this entrepreneurial background and didn't even know it." The lessons learned from observing his father's dedication and the demands of running a farm have stayed with him, influencing his career long after he left that life behind.

The Journey to G2

Tim's path eventually led him to co-found G2, a platform that has revolutionized the way businesses evaluate software. Today, G2 boasts over six million verified reviews and attracts around 200 million software buyers yearly. As Tim describes it, "If you've not heard of G2 in the last decade, you've probably been living in some sort of a bubble universe."

The transition from farm life to tech entrepreneurship may seem vast, yet Tim sees parallels between the two worlds. "I remember that morning when I was out there shoveling manure, and now I'm shoveling software reviews. No matter what you're shoveling, you've got to do it in a way that makes the customer happy."

Closing Thoughts

As we reflect on Tim's journey from the fields of Iowa to the forefront of the software industry, it's clear that every experience shapes who we become. Whether in the boardroom or on the farm, the core principles of hard work, dedication, and a customer-first mindset remain vital.

Great careers are not always planned. Janet Foutty has spent her life proving that the most meaningful paths are often discovered - one bold decision, one smart pivot, and one “work hard and don’t suck” moment at a time.

From her early days at Deloitte to becoming its chair, Janet shares the real operating principles behind an extraordinary leadership journey: why she looks for gaps instead of titles, how she builds trust by showing up fully for her team, and why the best leaders are often the ones who make room for other voices (not the ones who try to be the loudest in the room).

We break down the mindset that took her from operator to CEO to board chair, including:

• The three criteria she uses to decide whether a role is worth staying in,
• Why “lowercase I” impact often matters more than grand strategy,
• How to spot dumb systems before they waste years of everyone’s time,
• What great boards actually owe their CEOs, and
• The early signals that a leader may be wrong for the company’s next chapter

Janet also opens up about the decisions that looked irrational from the outside but turned out to be pivotal, including launching Deloitte Digital and stepping away from a role most people would have clung to. Along the way, she explains why she believes the future of work, especially in the age of AI, is one of the most important issues facing businesses and society right now.

If you care about leadership, career growth, board dynamics, or the future of work, this conversation is packed with practical wisdom you can actually use - whether you’re building a company, leading a team, or trying to figure out what your next chapter should be.

Alex Kerr has built his career around sports, data, and figuring out what actually creates value.

In this episode of Boardroom Blitz, we talk with the Trajektory founder and CEO about the lessons he carried from the baseball diamond into the boardroom, building a company in the sports industry, making decisions with imperfect information, and why good data still requires good judgment.

We also tackle one of the great intellectual debates of our time: why Star Trek is science fiction and Star Wars is basically fantasy with spaceships.

Leadership, entrepreneurship, sports, analytics, and a healthy amount of nerd nonsense. Pretty much our kind of conversation.

In this episode, Jeremie Bacon interviews Ryan Eisenman, CEO of Arch, about building a fast-growing fintech company in the private markets space. They discuss trust-building, scaling challenges, the role of in-office culture, and the strategic use of AI to automate tedious tasks while maintaining high-quality service.

Key topics

• Trust-building with conservative clients
• Scaling from zero to 640 clients
• In-office culture as a competitive advantage
• AI strategies for automation and oversight
• Venture capital support and long-term vision

From corporate lawyer to frozen-food founder, Emily Groden has taken a decidedly unconventional path to entrepreneurship.

In this episode of Boardroom Blitz, Emily, the Founder and CEO of Evergreen, shares how her search for a quick, nourishing breakfast for her daughter inspired her to begin making waffles in her own kitchen. That personal project eventually became Evergreen, a rapidly growing frozen breakfast brand built around whole grains and recognizable ingredients.

Emily takes us behind the scenes of the company’s origin story, the transition from idea to retail shelf, and the persistence required to build a consumer packaged goods brand from the ground up. She also opens up about raising venture capital, what founders should consider when choosing financial partners, and the lessons she has learned while scaling Evergreen.

Whether you’re building a business, considering outside investment, or simply curious about how an everyday consumer problem becomes a national brand, Emily’s story is packed with candid insights and entrepreneurial inspiration.

Learn more about Evergreen at https://eatevergreen.com/.

In the debut episode of Boardroom Blitz, Betsy Ziegler, CEO of 1871, joins Garry and Jeremie to talk about career pivots, personal agency, and what it really takes to build a life and career that fit.

From McKinsey to higher education to leading one of the country’s most important innovation hubs, Betsy’s path proves that leadership is rarely linear, reinvention is not failure, and sometimes the most strategic move is finally admitting you want something different.

Learn more about 1871 at: www.1871.com