From Start-Up to Grown-Up

In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Daniel Yanisse, co-founder and CEO of Checkr, to discuss the exhilarating rise and the challenges of sustaining a high-growth company. Checkr revolutionized the background check industry, scaling from a $1M revenue run rate in just three months to processing millions of background checks annually. But with hypergrowth came intense operational, cultural, and leadership challenges.

Daniel shares how he navigated:

• Hiring at hyperspeed—and why some employees quit on day one.
• The "hangover" after hypergrowth—losing key executives and investor pressure.
• How to hire and retain top executives—and avoid common leadership hiring mistakes.
• Revising a company mission to balance fairness and safety while scaling.
• The "Fly High, Fly Low" leadership approach—balancing strategy and deep operational insights.

This episode is packed with real-world lessons for founders, CEOs, and startup leaders facing the challenges of rapid growth, leadership transitions, and market shifts.

🎧 Listen now and learn how to build and sustain a high-growth company.

 Timestamps & Key Topics

00:00 – Introduction

02:30 – The Early Days of Checkr

06:20 – The Downside of Hypergrowth

08:45 – Facing Leadership Challenges & Executive Turnover

15:30 – Hiring and Managing Executives

21:00 – Redefining Checkr’s Mission: Fairness vs. Safety

28:00 – Leadership Lessons & Overcoming Challenges

39:00 – Confidence, Imposter Syndrome & Founder Loneliness

45:00 – Final Advice for Founders

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Peter Attia, MD, is the founder of Early Medical, a medical practice that applies the principles of Medicine 3.0 to patients with the goal of lengthening their lifespan and simultaneously improving their healthspan. He is the host of The Drive, one of the most popular podcasts covering the topics of health and medicine. Dr. Attia received his medical degree from the Stanford University School of Medicine and trained for five years at the Johns Hopkins Hospital in general surgery, where he was the recipient of several prestigious awards, including resident of the year. He spent two years at the National Institutes of Health as a surgical oncology fellow at the National Cancer Institute, where his research focused on immune-based therapies for melanoma.

Learn more about Peter here | Website

https://www.peterattiamd.com/

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Isabelle Freidheim is the founder and managing partner of Athena Capital. She is the youngest chairman of a publicly traded company in the U.S. In her role as managing partner of Athena Capital, Freidheim oversees the company's strategic direction and leads its efforts in identifying and investing in technology companies.

Freidheim is an entrepreneur and investor with more than 15 years of experience in venture capital, private equity, SPACs and IPOs. She founded Athena in 2020. Athena Capital invests at the intersection of private companies preparing to go public or considering M&A exits. Athena’s platform includes board members of Fortune 100 companies and CEOs, Fortune 500 companies, company founders and investors. Freidheim is one of Inc's 250 Female Founders in 2024, a member of The Council on Foreign Relations and an alumna of Fortune's Most Powerful Women.

Find out more about Athena Capital | Website

https://www.athenacap.com/

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During his 15+ years at Amazon, Ethan Evans helped invent Prime Video, Amazon Video, Amazon Appstore, Merch by Amazon, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. He led global teams of over 800 and holds more than 70 patents. Ethan has reviewed 10,000+ resumes, conducted 2,500+ interviews, made 1,000+ hires, and was an Amazon Bar Raiser and Bar Raiser Core Leader, responsible for training and maintaining Amazon's group of interview outcome facilitators.

Ethan helped advocate for and draft the Amazon Leadership Principle (LP) “Ownership” — the words, “They never say ‘that’s not my job.’” are Ethan’s (read the story).

At Amazon, Ethan promoted 8 reports from Senior Manager (Amazon L7) to Director (Amazon L8), contributed to 25+ Director promotions, hired 10+ Directors internally and externally, and drove the promotion of 3 engineers to Principal. Of his former reports, 2 are current Amazon VPs (L10) and 5 are C-Suite outside Amazon.

Ethan retired from Amazon as a Vice President in September 2020 to pay forward his good fortune.

Prior to Amazon, Ethan spent 12 years at 3 startups.

Ethan now teaches leaders to become true executives. Subscribe to Ethan’s newsletter, Level Up, for ongoing career advice, and consider joining the Level Up Career Community. Ethan also offers a range of Leadership Development Courses (live online and on-demand) that go in-depth on topics like “Breaking Through to Executive,” “Managing Up Successfully,” “Leadership Networking,” and more. If you’d like to connect, you can find Ethan on LinkedIn.

Contact Ethan on his website for inquiries about corporate training, speaking requests, and podcast appearances. | Website
https://www.ethanevans.com/

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Robert Glazer is the Founder and Chairman of the Board of global partner marketing agency, Acceleration Partners. He is also the co-founder and Chairman of BrandCycle. A serial entrepreneur, Bob has a passion for helping individuals and organizations build their capacity to elevate.

Learn more about Bob and his latest book, Rethinking Two Weeks' Notice | Website
https://robertglazer.com/two-weeks/

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Chip is the founder of the Modern Elder Academy (MEA), where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico, and forthcoming campuses in Santa Fe, NM. His five books have made him a leading authority at the intersection of psychology and business. 

Chip had tons of wisdom to share in this talk, including how to use regret as fuel for the future, what founders can learn when they shift their identities, how to manage people older than you, what Chip learned from the people that he mentored, and his favorite interview question. 

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 Resources Mentioned

• Finish Big: How Great Entrepreneurs Exit Their Companies on Top: https://bit.ly/3jtlA2N
• Life Is in the Transitions: Mastering Change at Any Age: https://amzn.to/3HFPjOa
• Wisdom at Work: The Making of a Modern Elder: https://bit.ly/3YjOxwQ

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• Website: https://chipconley.com/
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• LinkedIn: https://www.linkedin.com/in/chipconleysf/
• Facebook: https://web.facebook.com/chipconleyauthor

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Gary Vaynerchuk, also known as "GaryVee," is a serial entrepreneur, the Chairman of VaynerX, and 5x New York Times Best Selling Author. He is a leading global mind on what's next in culture, relevance, and the internet. Gary possesses an uncanny ability to recognize trends and patterns early to help others understand how these shifts impact consumer behavior. He is one of the most forward-thinkers in business. Gary's approach sits at the intersection of business and culture. He keenly understands how to bring brand relevance to the forefront.

“It's not a hokey thing to say you have to enjoy the journey. It's the only sustainable thing.” 

That’s one of the wisdom bombs from my latest guest on From Start-up to Grown-up, the legendary  Gary Vaynerchuk- Chairman of Vayner X and the author of his brand new book, Day Trading Attention.

Here are a few more of the many great takeaways Gary offered during our discussion:

“Chasing the short-term is the number one strategy that makes people fail.”

“Entrepreneurship is a constant game of losing with occasional wins.”

“There’s nothing that happens on earth that doesn’t start with attention.”

Learn more about his book, Day Trading Attention | Website
garyvaynerchuk.com

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Colin Bryar is a business advisor and technology leader whose career has focused on optimizing business strategy, technology, and operations. He is a former top-level executive at Amazon, where he spent more than 12 years – much of it in the early aughts during the company’s period of unmatched innovation – serving as a tech VP, leading the operations for IMDb.com, as well as shadowing and working directly with Amazon CEO Jeff Bezos to help with all aspects of Amazon's business including strategy, technology, and operations.

Bryar is also the co-founder of Working Backwards, LLC where he coaches and advises executives at both early stages and established companies around the globe, helping them to implement the management practices developed at Amazon. He also serves as an advisor for Singapore-based online marketplace, Carousell.

Learn more about Colin | Website

https://www.workingbackwards.com

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David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man.

He writes regularly on HEY World and speaks on The REWORK Podcast. 

Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web framework he created in 2003, and continues to develop to this day. Some of the more famous include Github, Shopify, Airbnb, Square, Coinbase, and Zendesk.

For my newest episode of From Start-Up to Grown-Up, I talk with David Heinemeier Hansson, Co-Founder of 37signals, to explore his journey of innovation, remote work, and unconventional management.

Learn more about DHH | Website
https://dhh.dk/

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Shegun Otulana is a seasoned entrepreneur, advisor, mentor and investor. Drawing from his experience as a bootstrapped startup founder who found incredible success, his mission is to empower the next generation of builders by sharing his lessons learned to guide their entrepreneurial journeys. In addition to mentoring founders in his community – many of whom have gone on to launch successful companies – he also enjoys sharing his insight with startup leaders, business associations, academic institutions and other growth-minded groups.

In 2013, Shegun founded TheraNest and its parent company, Therapy Brands, a software platform for mental, behavioral, substance and physical rehab providers and organizations. In 2021, he exited the business for $1.25 billion, the largest software exit on record in the state of Alabama.

Prior to establishing Therapy Brands, Shegun founded Zertis Technologies, a computer software consultancy company. Today, he continues his “idea lab” approach as the Founder of Harmony Venture Labs (HVL), an idea and growth studio that owns and operates a family of technology companies.

In this powerful episode of From Start-Up to Grown-Up, I sit down with Shegun Otulana, who bootstrapped his way from Nigeria to building a $1.25B healthcare tech company in Birmingham, Alabama.

What struck me most about Shegun's journey?

➡️ The power of constraints as blessings - limited funding forced profitable growth from day one

➡️ Culture needs rituals - it's not enough to have values, you must memorialize and celebrate them

➡️ Leadership growth requires vulnerability - others see you differently than you see yourself

One of my favorite insights: "Your nature is your nature, but you need to find people who complement what you don't bring to the table." 

Shegun openly shared how he learned to build strong remote teams by finding cultural champions when that wasn't his natural strength.

When Shegun could only raise $250,000 in 10 months for his healthcare SaaS company, he turned that constraint into motivation. 

Without the luxury of burning cash, he had to build profitably from day one. 

Rather than seeing limited capital as a barrier, he viewed it as a blessing that forced disciplined growth - a mindset that ultimately led to a billion-dollar exit.

It's about intentionally designing incentive structures that make your team feel safe to experiment and learn.

Learn more about Shegun | Website
https://shegunotulana.com/

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