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Entrepreneurship, fundraising, and practical advice for startup founders :: with Troy Henikoff

This week I’m excited to share an in-depth conversation with Troy Henikoff  (https://www.linkedin.com/in/troyhenikoff/, https://www.mathventurepartners.com/ ) about his entrepreneurial story and path into startup investing. Troy is one of the most amazing and inspiring people I know. I first met him when I moved to Chicago in the mid-2010s, and his generosity, enthusiasm, and support for founders has been consistently admirable and contagious. After an extended introduction where he shares his story, we walk through practical validation, execution, and funding advice for early stage founders.

You can watch this episode below or listen on Apple Podcasts, Spotify, Google Podcasts, or wherever you get your podcasts.

In this episode we cover the following:

2:12 - Extended Troy intro: his journey as an entrepreneur, starting and selling multiple companies, working for his acquirers, angel investing in new companies, starting a fund (Firestarter Fund) and accelerator (Excelerate Labs), teaming up with Techstars, and ultimately starting MATH Venture Partners.

26:20 - What fuels Troy’s “Give First” ethic? Many who have worked with him over the years have noticed his exceptional and inspiring generosity, where did that come from? What’s behind that?

30:21 - Going back to Troy’s early companies, once he noticed a semblance of Product-Market Fit, how did Troy navigate the dance between managing growth and product?

40:20 - What advice does Troy have for someone who has a day job and has an idea for a startup? (Check out the Jobs to Be Done and Clayton Christensen Milkshake, specifically this short video)

45:25 - In the startup landscape, is “Business to Business” (B2B), “Consumer” (B2C), and “Marketplaces” roughly the broad categories out there, and how do entrepreneurs know whether their startup in each model is “validated”? (It’s an art form, and “it depends”, but a key thing to look for is engagement)

51:03 - How should entrepreneurs with a validated idea - or idea they think is validated - go about the process of practically building the product?

55:54 - What advice does Troy have for founders looking for a technical co-founder?

1:00:40 - When a founder finds a potential technical co-founder, how should they practically engage? What are the first steps? How do they set up clear communication and expectations?

1:08:22 - How should founders think about fundraising? Who are the players and what are the stages?

1:13:25 - A word on financial modeling and the importance for founders to build one (Troy and I co-wrote an article series here on Financial modeling, including a practical example).

1:17:53 - Where can people find out more about Troy, MATH Venture Partners, and the videos he’s put together? https://www.mathventurepartners.com/ 

Additional resources mentioned:

Pot of gold: https://www.mathventurepartners.com/blog/2018/12/6/math-101-pot-of-gold // “if you show an investor a big pot of gold and a low-risk path to getting that pot of gold, he/she is going to invest.”

Download Troy’s deck on financial modeling here.

Detailed videos on financial modeling: