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In the last two years, Blaine has become one of the most prolific angel investors in the country. He previously founded Student Brands which he bootstrapped with his co-founders and ran as CEO then chairman through acquisition by Barnes and Noble in 2017. Blaine also co-founded Solve which completed the summer 2017 Y Combinator batch and was acquired later that year. Beyond his success as a founder and investor, Blaine is a deeply thoughtful, humble, and curious human willing to speak openly about numerous aspects of the founder journey and his experience on the investor side. If you have ever felt like investors are ‘the other’ or out of reach, this conversation may be deeply helpful.

Gaurav Bhattacharyya (Co-Founder and CEO of Involve.Ai) shares the very human side of his leadership journey over the last 18 months. Involve recently raised a $16M round, but a year ago, the founders considered shutting down the business. We explore impostor syndrome, navigating hard decisions and conversations, and inviting your team and board into the company's most difficult questions.

Sarah is the founder of S’well, maker of arguably the world’s best water bottles. Sarah and I talk about her realization she no longer wanted to stay in the CEO role at the company she founded as well as her decision to eventually conduct the search for a new CEO openly on social media. We also explore leading a team through transition and how to find support in your own big questions.

Lindsay Blakeley is the managing editor of Inc.com and LA’s Inc. bureau chief. I met Lindsay at an investor-hosted dinner in Beverly Hills a couple of years ago. We realized we had a shared curiosity regarding the human side of startup life. That curiosity resulted in a piece in this September’s Inc. but also in an ongoing conversation around topics surrounding the founder journey. Many of the founders I spend time with as a coach face shared challenges including depression, anxiety, burnout, and questions of whether they are enough (themes I too faced in my own time as a founder and CEO). Lindsay has spoken with hundreds of founders over her years as a reporter. She is therefore in an interesting position to help us normalize parts of the founder experience that can be hard to see clearly in our own heads. Lindsay also shares some practical advice on how to connect with reporters and share your own story in an authentic way.

Trevor Owens is an expert in Lean Startup Methodology, which I believe is the best way for any startup or company to find product-market fit for any new idea. Trevor is the author of the bestselling book on applying Lean Startup methods in large organizations, The Lean Enterprise: How Corporations Can Innovate Like Startups. Trevor’s work has been featured in national media outlets including Forbes, Bloomberg, Fast Company, Business Insider, Mashable, and others. He's been a featured guest speaker at Princeton University, Columbia University, the United States White House, and worked with companies around the world including General Electric, Amazon, Microsoft, Huawei, United State Postal Service, and many others.  Trevor was previously the founder and CEO of Lean Startup Machine and Javelin and is currently working on a new product which he talks about in the episode. We explore lean but also major life and leadership topics including burnout, grief, loss, layoffs, running out of money, the pressure to lead well, and the art of starting over. 

In this episode we welcome Amir Salihefendic. Amir is the founder and CEO of Doist, maker of one of the world’s most widely used task-management apps, ToDoIst. Amir bootstrapped Doist to millions of customers and tens of millions in revenue. But that’s not why I’m excited for you to meet him. I’m excited because of the honestly and openness he brings to some of the biggest questions that haunt each of us. What makes me valuable? How do I know if I’m doing or achieving enough? What is enough? What actually makes my life valuable?

I am excited today to welcome Warren Shaeffer, co-founder and CEO of Knowable. Knowable is an audio-based learning platform backed by Andreessen Horowitz, First Round Capital, and Upfront Ventures. Warren and I discuss leading a startup during the pandemic, cofounder challenges and successes, and practices for managing your own mental well-being while leading through uncertain times.

Meg is the founder and CEO of one Rocksbox, one of the category leaders in DTC and online jewelry. Rocksbox has faced challenges common to many companies right now including having their distribution center shut down by shelter-in-place orders, a sudden unavailability of new capital, and a difficult layoff of many team members. Meg shares her story about these very recent challenges with tremendous humility, clarity and grace.

I am excited to welcome my own longtime coach and good friend Jerry Colonna. Jerry spent years as a venture capitalist, starting Flatiron Partners with Fred Wilson in 1996 before turning to coaching and eventually founding well-known coaching group Reboot. Jerry and I explore leading through a crisis you may not feel quite ready for, how to manage our own psychology, and finding freedom from the notion that leaders must have it all figured out.

Today, I am excited to welcome my good friend Yanda Erlich to the show. Yanda is prolific angel investor, having backed companies including Thumbtack, Masterclass, and CircleUp, and managing director at Coatue where he focuses on early stage enterprise investing. He’s also a 4-time venture-backed founder. So he knows a lot about both sides of the fundraising table. An all around brilliant human and total mensch. Can’t wait for you to meet him. 

Today I am excited to welcome my good friend Isaac Oates. Isaac is the founder and CEO of Justworks. A 580 person startup based in New York City, the US epicenter of the current crisis. Isaac and I chat preparing a team for fully remote, leading in crisis, and running a company while parenting in quarantine. You’ll learn tactics for communicating in times of crisis, for supporting a team in a newly dispersed environment, and for getting through times when capital is tight. You’re going to love Isaac!