Skin in the Game VC Podcast

Latest Episodes:

Stuart Bertron - Assessing Investment Situations Aug 13, 2019

Show notes

The investments industry is wrought with decisions—and they’re never easy to make.

Stuart is a native of Tampa, Florida. He moved around, went to school at UVA, but eventually made his way back home to Tampa. Ever since then, he’s been an active investor in technology companies. Some of his investments were incredibly successful and some were not. Each investment he made, however, provided him with new, valuable experience to learn from for the future.

On today’s episode, Stuart shares both these successes and failures. He shares his personal journey as an investor along with some of the nitty-gritty details of how he makes those big decisions and his own journey along the way.

So get ready to learn some new strategies regarding making investments and what to watch out for.

Some Questions I Ask:

When and how did you start angel investing? (4:27)
What do you look for in an investment? (5:50)
What deal size do you look for? (8:00)
What red flags do you look for when considering an investment? (11:12)
How do you interpret the market when making investments? (12:57)
What’s the most important part of due diligence? (20:31)

In This Episode, You Will Learn:

How Stuart made his first investment. (2:27)
Why focusing on the entrepreneur when choosing an investment is crucial. (5:55)
Why it’s important to be as real and authentic as possible in investment conversations. (11:24)
How the market determines the potential for the business you invest in. (13:05)
When to put more money into a company, and when to shut it down. (15:26)
Why some of Stuart’s investments failed. (16:01)
About the roles of communication and coachability in the investment industry. (19:52)

More about Florida Funders:

Website

Our Investment Process

Hosted on Acast. See acast.com/privacy for more information.

Jake Seid – Keep Up Your Momentum May 21, 2019

Show notes

Sometimes the most thrilling investments are ones that will disrupt society.

Disruptive investments—such as investments in transformational technologies that utilize applied artificial intelligence—oftentimes turn out in one of two ways. They can soar—like Apple or Microsoft—or they can tank.

Today’s guest, Jake Seid, says that when downturn happens, you can’t lose your momentum. Sometimes the best companies are built after these downturns—don’t forget that.

Jake is the managing director at Stone Bridge Ventures. He’s a venture investor focused on investments around the Bay Area in California, but he also invests nationally. Generally, he focuses on investing in disruptive technologies.

So get ready to learn from some of Jake’s hits and misses in investing so far.

Some Questions I Ask:

How did you first get involved in angel investing? (2:30)
What’s important to you in a company that you want to invest in? (3:14)
What was your biggest miss? (5:19)
What do you look for in founders? (8:15)
Will you make an investment even if you predict a need to change the company’s top leadership within a couple of years? (10:36)
What do you hope to hear from a company regarding their exit strategy? (18:57)
Where do you get your best deal flow? (21:51)

In This Episode, You Will Learn:

Where Jake received strong mentorship in investing early on in his career. (2:34)
What makes a company worth investing in. (3:26)
How to create defensibility. (4:34)
About Jake’s biggest mistake in his career. (5:25)
About the pros and cons of a founder and a founding team. (8:24)
How investors can add more than monetary value to the company. (13:20)
Why Jake is willing to take risks on technology. (15:37)

Connect with Jake:

Twitter

AngelList

More about Florida Funders:

Website

Our Investment Process

Hosted on Acast. See acast.com/privacy for more information.

Zach Coelius - From Entrepreneur to Investor May 07, 2019

Show notes

Investing in your first business can be incredibly daunting.

There are so many unknowns and so many what if? questions running through your head. It’s the same situation for both the entrepreneur and the investor. Entrepreneurs and investors alike have a goal in mind—and they need the other person in order to get there. It’s risky, but sometimes it’s totally worth it in the end.

Today’s guest is Zach Coelius. Zach has worked on both sides of the story. He is a four-time entrepreneur, but now that he’s sold his last company, he shifted to full-time angel investing. In this episode, Zach tells us all about his experiences of getting started in investing, what his strategies are, and how he has become so successful.

So get ready to learn about Zach’s journey so far. Along the way, ask yourself: what will it take for me to get started?

Some Questions I Ask:

What do you like better: being an entrepreneur or being an investor? (2:04)
How did you first get involved in angel investing? (3:34)
Where do you get your deal flow in? (7:10)
What are you looking for in an investment? (8:51)
When investing, when do you look for in the founder of the company? (11:54)
There’s a lot going on in technology today. What are you interested in? (14:57)
What red flags do you look out for in investing? (16:28)
How much do you get involved in your investments? (21:55)

In This Episode, You Will Learn:

About both the dark and light sides of entrepreneurship and investing. (2:07)
How Zach transitioned from entrepreneurship to angel investing. (3:38)
About how Zach’s “lazy-helpful” work with Silicon Valley changed the course of his career. (7:14)
How entrepreneurship experiences can change investment behavior. (8:58)
Why the founder is what can make or break the choice to invest. (12:10)
Why Zach gets as involved as possible in his investments. (22:00)
Why pitch competitions are ineffective and inefficient. (24:12)

Resources:

Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley by Antonio Garcia Martinez

Connect with Zach:

AngelList

More about Florida Funders:

Website

Our Investment Process

Hosted on Acast. See acast.com/privacy for more information.

Alex Sink - To risk, or not to risk? Apr 15, 2019

Show notes

Have you ever played with the idea of investing?

Are you an entrepreneur searching for an investor?

What’s stopping you?

Here at Florida Funders, our goal is to scour the state of Florida, searching for the very best early-stage technology companies to find, fund, and help build up. We are dedicated to changing Florida from the “Sunshine State” to the “Startup State,” making this a great place to start and build a business.

On today’s podcast, we talk to Alex Sink. Recently, Alex decided to shift her career from politics to helping entrepreneurs bring their fantasies to reality. In this episode, we talk all about her investment journey, what her ideal investment is, and what red flags she watches out for.

What will it take for you to get started?

Some Questions I Ask:

· How did you get involved in investing? (3:32)

· What technology or business models do you like that influence your investing habits? (10:56)

· What deal size do you look for? (13:46)

· How do you look at follow-ons? (17:03)

· What do you think of pitch competitions? (21:48)

· How involved do you like to get in an investment? (23:33)

In This Episode, You Will Learn:

· About Alex’s transition into investing and her early-stage strategies. (3:44)

· How to figure out what to invest in as a beginner. (11:06)

· How Alex chooses what to invest in. (13:54)