From Start-Up to Grown-Up

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.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!

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 | Websitehttps://www.workingbackwards.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!

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 | Websitehttps://dhh.dk/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!

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!