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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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

Follow Chip Conley on:

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

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Follow Alisa Cohn on

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• 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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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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• Website: http://www.alisacohn.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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• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

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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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• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

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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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• Website: http://www.alisacohn.com

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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 one
• Holding to an unchanging vision
• Work 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 | Website
https://bebravehealth.com/

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• 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)

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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 | Website
https://www.onehopewine.com/

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• 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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