From Start-Up to Grown-Up

• #88: From Startup to Grown-Up: Eddie Kim, Co-founder and CTO of Gusto - Wearing different “hats” as a leader; learning to get his hands off the keyboard and enable others instead; and how to build a growth mindset

  Eddie Kim is the CTO and cofounder of Gusto, which serves 400,000+ small and medium-sized businesses nationwide by helping them onboard, pay, insure, engage, and provide benefits for their teams, in one integrated, friendly, and easy-to-use platform. Eddie’s career has been shaped by chance encounters, a passion for software, and a deep commitment to growth. Before Gusto, he launched his first company—an experience that ultimately led him to reconnect with his future co-founder, Josh Reeves.In this episode, Eddie opens up about co-founder dynamics, leadership struggles, scaling a company, and the surprising tools he uses to stay aligned with his team.Episode Highlights & Timestamps🔹 [00:00] - The Decision-Making Process of a Leader🔹 [02:00] - The Origin Story of Gusto: A Half Marathon That Changed Everything🔹 [06:00] - Co-Founder Dynamics: How Eddie, Josh, and Tomer Divided Leadership Roles🔹 [10:00] - Managing Ego: Accepting the CTO Role Instead of CEO🔹 [12:00] - Hands Off the Keyboard: How Eddie Transitioned from Engineer to Leader🔹 [15:00] - The Role of Mentors: Lessons from Jeremy Stoppelman (Yelp) & Drew Houston (Dropbox)🔹 [17:00] - Breaking Stereotypes: Being an Asian Founder of a Unicorn Startup🔹 [20:00] - The Role of Company Values in Decision-Making & Hiring🔹 [24:00] - Encouraging Debate in an Organization & Aligning the Team🔹 [32:00] - Wearing Multiple Hats: The Skill Every Leader Must Master🔹 [38:00] - The Highs and Lows of Hiring Executives🔹 [40:00] - Gusto’s AI Initiatives: How AI is Revolutionizing Payroll & HR for Small Businesses🔹 [45:00] - Eddie’s #1 Advice for Founders: The Power of a Growth MindsetResources & References📖 Mindset: The New Psychology of Success – Carol Dweck🎙️ Listen to my previous conversation with Gusto Co-Founder & CEO Josh Reeves (Episode 58)Where to Find Eddie Kim🌍 Website: www.gusto.com🐦 Twitter: @edawerd💼 LinkedIn: Edward KimConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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• #87: How Daniel Yanisse Scaled Checkr to $700M+ and Overcame the Post-Hypergrowth Crisis

  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 Topics00:00 – Introduction02:30 – The Early Days of Checkr06:20 – The Downside of Hypergrowth08:45 – Facing Leadership Challenges & Executive Turnover15:30 – Hiring and Managing Executives21:00 – Redefining Checkr’s Mission: Fairness vs. Safety28:00 – Leadership Lessons & Overcoming Challenges39:00 – Confidence, Imposter Syndrome & Founder Loneliness45:00 – Final Advice for FoundersConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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• #86: Peter Attia, MD, Founder of Early Medical — improving your lifespan and healthspan, the centenarian decathlon, and the process of making major life changes (Repost)

  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 | Websitehttps://www.peterattiamd.com/Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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• #85: Isabelle Freidheim, Founder of Athena Capital — The benefits of being an only child, creating opportunities for women in finance, and unlocking hidden talent

  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 | Websitehttps://www.athenacap.com/Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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• #84: Ethan Evans, Executive Mentor and Former Amazon VP — Managerial myths debunked, how to create a safety net for your career, and why everyone should write online

  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. | Websitehttps://www.ethanevans.com/Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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