#71: Matt Reustle, CEO of Colossus — Lessons from a first-time CEO, how to analyze a career pivot, and the art of a great question

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 yourselfOne 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 | Websitehttps://shegunotulana.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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Jake Schwartz is a serial entrepreneur, investor and advisor. Until 2020, Jake Schwartz served at CEO of General Assembly (GA), the global leader in education and career transformation, which he co-founded in 2011. He grew GA to over 1,000 employees on five continents. In 2018, GA was acquired by The Adecco Group. Jake Schwartz co-founded and serves as Chair of Brave Health, a mission-driven company focused on expanding access to high-quality, affordable care for mental health and addiction. Jake Schwartz was named E&Y Entrepreneur of the Year in 2014 and one of Crain’s “40 under 40” in 2015. Jake holds a BA from Yale and an MBA from The Wharton School of Business at the University of Pennsylvania. He is a former CFA Charterholder.When you hear the founding story of any startup, it can often feel like it was destined.That the end was clear at the beginning and the founders held an unwavering gaze.We often think launching a successful company requires:Defining roles from day oneHolding to an unchanging visionWork through a clear path to get there.That's one way to do it!But what if there's another approach?What if building a successful startup isn't about following a strict formula, but about embracing serendipity and intuition?Jake Schwartz, Co-Founder and former CEO of General Assembly, didn't have a conventional playbook. Looking back a decade later, he felt like they were forming a band.Just get together, start creating, figuring things out as you go.What I took away from this discussion:Passion > perfect plan. Flexibility > rigidity early on. Evolution > clear vision.By following their intuition and leaning into serendipity, Jake and his co-founders discovered a unique formula for success.Learn more about Jake and Brave Health | Websitehttps://bebravehealth.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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Jake Kloberdanz is the founder of ONEHOPE, a pioneering wine brand with a mission to create a positive social impact. Under his leadership, ONEHOPE has donated tens of millions of dollars to over 40,000 non-profits and grown from zero to producing over one million bottles per year. The company boasts a world-class vineyard in Napa Valley and has garnered more than 30 wines with 90+ point ratings. Recognized as one of the fastest-growing private companies by Inc. Magazine, ONEHOPE has raised over $100 million in funding. Jake has been honored as a "Top 40 Under 40" by Wine Enthusiast and a "Top 30 Under 30" by Forbes. He serves on the boards of 8VC and After the Fire, and is a sought-after speaker, having presented at the UN Global Summit, TED, and leading universities like Stanford and MIT. A graduate of UC Berkeley's Haas School of Business and a two-time national rugby champion, Jake is an advocate for "Cause-centric Commerce," integrating purpose into business models.This new episode of From Start-Up to Grown-Up features an in-depth conversation with Jake Kloberdanz, the Co-Founder and CEO of One Hope Winery, who’s reshaping how business and philanthropy intersect. From selling wines out of a U-Haul to building a company that’s donated over $10 million to meaningful causes, Jake's story is nothing short of inspiring.Jake talks about his original idea to create “Girl Scout Cookies for adults” and how that evolved over time. He also talks about his evolution as a leader as the company overcame turbulence, how he learned the importance of clarity and how he developed his frameworks for communication. Learn more about One Hope Winery | Websitehttps://www.onehopewine.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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Susan McPherson is a serial connector, angel investor, and corporate responsibility expert. As the founder and CEO of McPherson Strategies, a communications consultancy focused on brands and social impact, she brings over 30 years of experience in marketing, PR, and sustainability communications. Susan is the author of The Lost Art of Connecting and a sought-after speaker at major events like the Massachusetts Conference for Women and Techonomy. She has contributed to outlets like Harvard Business Review and Fast Company and has appeared in NPR, CNN, and USA Today. Susan invests in and advises women-led startups and is involved in several boards and advisory groups, including The 19th News and Just Capital. This episode of From Start-Up to Grown-Up dives into the world of networking and relationship-building with Susan McPherson – a “super connector” who leverages her extensive network to help others and grow her own business, McPherson Strategies!Susan shares her insights on the significance of rekindling dormant ties, the benefits of dormant connections, and the importance of proactive outreach in networking.Susan started her company at the bold age of 48, reaching out to a staggering 500 people in her network, demonstrating the power of asking for help and the value in promoting others. She's full of practical tips - including hosting your own events collaboratively and keeping the conversation focused on what others need. We'll also hear about her smart approach to follow-up after events, employing the "ten touches rule" to keep her contacts engaged.Prepare to be inspired as Susan discusses her entrepreneurial journey, overcoming personal and professional low points, and the joy she finds in team growth and recognition. Stay tuned as we learn that it's never too late to start, it’s okay to be afraid of failure, and that, at times, success is serendipitous – often resulting from seeds we plant long before they bear fruit.Learn more about Susan | Websitehttps://www.susanmcp.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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Jeff Shiner is the CEO of 1Password, a leader in human centric security and privacy. Since joining in 2012, Jeff has grown the company from 20 people to a 900-employee global organization with a $6.8 billion valuation. Today, 1Password enables over 100,000 businesses and millions of individuals to navigate the digital world without fear or friction when logging in – and in less time. The company has been recognized on the Forbes Cloud 100 list and Quartz’s Best Companies for Remote Workers. Prior to joining 1Password, Jeff held leadership roles at IBM Canada and Rosetta and has a demonstrated history of growing technology companies. Jeff also currently serves on the Board of Directors of GenomOncology, a company that provides the healthcare community with data-driven insights to improve cancer care. Jeff is a noted speaker at events like Web Summit, Collision, and the C100. He also provides regular commentary to top-tier publications like Fast Company, Forbes, ZDNet, and VentureBeat, among others. When he’s not busy being a CEO, Jeff enjoys watching the 49ers, spending time on his tractor, and adding to his LEGO collection with his son – he’s the proud owner of more than 1,000 pounds of bricks!This episode of From Start-Up to Grown-Up features Jeff Shiner, CEO of 1Password, who offered an unguarded look into his journey scaling a company from 20 people to 1200 employees.This episode is particularly valuable for first-time founders, as Jeff covers how to mitigate the lonely job as a founder by making  smart hires, what you can do to cultivate a strong team through reflective hiring practices, and the activities that can ground you and give perspective.This is such a powerful and practical episode that will bolster all founders and leaders with resolve!  Learn more about 1Password | Websitehttps://www.1Password.comConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Seth is an entrepreneur, best-selling author, and speaker. In addition to launching one of the most popular blogs in the world, he has written 20 best-selling books, including The Dip, Linchpin, Purple Cow, Tribes, and What To Do When It's Your Turn (And It's Always Your Turn). His book, This is Marketing, was an instant bestseller in countries around the world. Though renowned for his writing and speaking, Seth also founded two companies, Squidoo and Yoyodyne (acquired by Yahoo!).By focusing on everything from effective marketing and leadership, to the spread of ideas and changing everything, Seth has been able to motivate and inspire countless people around the world.In 2013, Seth was one of just three professionals inducted into the Direct Marketing Hall of Fame. In an astonishing turn of events, in May 2018, he was inducted into the Marketing Hall of Fame as well. He might be the only person in both.Imagine a world where people work where they are respected, where the work - not the employee - is thoughtfully criticized, and where managers create the conditions for employees to do the best work of their lives. Seth Godin does a deep dive on all of these and so much more in our conversation, sharing concepts from his brand new book The Song of Significance that reimagines what work and leadership can be.Find out more about Seth | WebsiteConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

David is Nash Squared's Group Technology Evangelist. He crafts podcasts, hosts video debates, speaks, moderates conferences, and chairs keynote stages. He's a passionate advocate for technology, dissecting its challenges and opportunities. David has worked at Nash Squared since 2007, where he has developed a deep understanding of the technology and talent markets. Recognised as Computing's Digital Ambassador of the Year (2018), he brings a wealth of experience and knowledge to every conversation. Since 2015 he has been editor and host of Tech Talks, a show about leadership and technology currently ranked as one of the most popular podcasts in the world.David Savage is this episode's guest, who reinforces why it’s so important to realize that trusting ourselves is a skill. And like all skills it can be developed! In addition to learning about trusting yourself, you’ll also hear from David how to become an “intrapreneur,” the importance of establishing consistent behavior, and how that applies to strengthening our personal branding.Learn more about David and Tech Talks | Website https://www.nashsquared.com/techtalksConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Kim Scott is the author of Radical Respect and Radical Candor. Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google.Being able to hold a candid and caring conversation with someone is an essential part of leadership.  My next guest on From Start-Up to Grown-Up is Kim Scott, bestselling author of Radical Candor and her new book, Radical Respect.Kim delivers a masterclass in building respect and kindness as the foundation of a company’s DNA with several strategies you’re going to want to use immediately.You’ll learn how to create an environment where employees feel safe. You’ll also learn that empowering yourself and your employees to challenge openly and diplomatically can lead to building a successful company.Learn more about Kim | Websitekimmalonescott.comConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Matt Reustle is currently the CEO of Colossus, a business that creates, curates, and distributes top-quality content for investors and entrepreneurs. He is the primary host of the Business Breakdowns podcast. Prior to Colossus, Matt worked in institutional investing. Most recently on the investment team at Raven Capital Management. Matt spent the first decade of his career at Goldman Sachs splitting his time between the Sales & Trading and Research divisions.If you’re thinking about a career pivot, if you’re trying to be a great leader in your company, or if you’re interested in podcasting, check out this great episode of From Start-up to Grown-up with Matt Reustle. Matt is the CEO of Colossus Media and host of the  podcast Business Breakdowns.Matt shares so honestly why leadership isn’t just about wins but about creating sustainable systems of growth and communication, how empathy is foundational for meaningful connections, and why there is an unlimited amount of friction running a company and how to find balance.Learn more about Colossus | Websitewww.joincolossus.comConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Mike Michalowicz is the entrepreneur behind three multimillion-dollar companies and is the author of several business books, including Profit First, Clockwork, The Pumpkin Plan and his newest book, All In.Mike is a former small business columnist for The Wall Street Journal and business makeover expert for MSNBC. He regularly travels the globe as an entrepreneurial advocate.We are going all in on the newest episode of From Start-Up to Grown-Up with author and entrepreneur Mike Michalowicz!Mike is a great story-teller and you’ll laugh out loud and come away with some great wisdom. Mike shares  practical exercises for team retention, how to come back from rock bottom, and the right way to hire people - interviews are over rated!You’ll also learn from his personal stories about the value and power of having an array of mentors, why companies thrive when leadership focuses on the human experience for both clients and employees, and how to build stamina to succeed as an entrepreneur.Learn more about Mike at Website | mikemichalowicz.comhttps://www.mikemichalowicz.comConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!