Skin in the Game VC Podcast

Latest Episodes:

Adam Struck - New Lands of Opportunity Dec 22, 2020

Show notes

Just like Florida is known for strawberries and tourism, LA is currently most famous for Hollywood – but things are gradually changing. The technology landscape is constantly growing and although LA has become a huge market, it still feels young. This means there are, yet, a lot of opportunities for angel investors to practice the art of venture capital in the right way, and grab their share of the market.

Adam Struck is a Floridian but he is currently living in LA with his family. Through his company, Struck Capital, he supports young founders providing core technology innovation to tackle the world’s largest problems. Adam and his team of investors focus on seed investments into companies led by visionary technologists.

Adam is a very successful young man who was named the Forbes 30 Under 30 Most Influential People – and in today’s episode, he is going to share his journey from being a lawyer to dedicating himself to transform LA into a place known for technology. We dive deep into his mindset and Struck Capital’s mission, as well as some successful deals he’s had over the years.

Tune in, to learn more about the changing landscape of LA and the investment opportunities you can find there.

Some Questions I Ask:

After you left the law firm, did you go right on to start your own firm? (03:57)
Tell us more about the journey at Struck Capital. What was your vision from the beginning? (07:31)
How did you get to move to LA? (08:42)
What is the main way you’re able to help founders grow their business? (15:08)
How did you find out about the Postmates deal? Are you still in it today? (17:35)
Have there been any investments that you passed on that you look back on and they really took off? (19:43)
What stage are you typically investing in? (21:46)
What do you see as the innovation and the opportunities in your area that you tend to look at? (25:00)

In This Episode, You Will Learn:

Adam’s journey from lawyer to being a venture capitalist. (01:20)
The entrepreneurial history of Adam’s family. (02:54)
The advantages of doing SPVs – Special Purpose Vehicle. (10:12)
The landscape in LA, in terms of tech companies. (11:07)
The reason Struck Capital was able to capture a lot of market share in a short time. (12:39)
The typical Struck Capital cheque size for investments. (22:28)
The partnership between Adam’s company and Leonardo DiCaprio’s platform. (23:33)
Adam’s advice for investors. (27:00)

Connect with Adam Struck:

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Jason Calacanis - Be Venture Worthy Sep 24, 2020

Show notes

Jason Calacanis is an entrepreneur, author, podcaster, and angel investor. He’s invested in more than 150 companies, including four multi-billion dollars “unicorns.” His story of investing in Uber is the stuff of investor legend. He’s also built and sold multiple companies for tens of millions of dollars and hosts the popular podcast “This Week in Startups” where he and a rotating group of guest experts bring you the weekly take on the best, worst, and interesting stories from the world of entrepreneurship.

As an entrepreneur turned successful angel investor himself, Jason knows how to spot a product that was crafted for growth. He’s had a front row seat to the way that both startup investing and working for startups is evolving in light of Covid.

exactly what he needs from his founders - and keeping him in the loop with regard to the health of your business is crucial. In today’s episode, he discusses why he’s eyeing a potential move outside of Silicon Valley, what it takes to make a truly remarkable product, why angel investors should ask for a board seat – contrary to what many people believe – and what types of companies to avoid if you’re just starting your investing journey.

Jason knows his game, so check out this episode to learn more about his thoughts on what’s happening with the current investment landscape, how to keep your investments close, and finding startups that are worth your investment.

Some questions I ask:

How did you get started in angel investing, and what were you doing prior? (06:05)
What’s the one thing you look for in founders? (12:26)
At which stage do you like to invest? (14:04)
How many boards do you sit on? (23:23)
What do you think the future of crowdfunding is? (30:03)
If you look at the game-changing technology that’s coming on board these days, are there certain ones that you are most excited about? (41:45)

In this episode, you will learn:

The changes the pandemic has brought in terms of doing business and closing deals. (02:27)
The story of Uber – what it was originally and how Jason ended up investing in it. (08:13)
How Airbnb was a unicorn that most people thought it was a bad idea. (10:46)
The types of companies you should avoid investing in if you’re a new angel investor. (14:36)
Jason’s four-bet strategy when he’s investing in a company. (16:18)
The importance of monthly monitoring your portfolio of investments. (18:30)
The two things Jason requires founders in their term sheets: to receive monthly updates and to have the option of a board seat. (21:34)
How regular board meetings can help founders when they’re discussing with investors. (22:10)
The global trend around risk and the importance of investing no more than 20% of your income average in startups. (31:50)
The advantage of collaborating with an Angel Group. (40:13)
Jason’s advice for people who want to venture into the podcasting world. (45:06)

Connect with Jason

LinkedIn
Email: jason@calacanis.com
Angel University
This Week in Startups Podcast
Book: Jason Calacanis – Angel: How to Invest In Technology Startups – Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

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Jeff Vinik - Integrity and Persistence: The Two Traits Every Founder Should Have Sep 10, 2020

Show notes

All successful founders, entrepreneurs, or business people have two things in common: integrity and persistence in always getting better at what they’re doing - and these are two traits that most angel investors look at when they’re considering to financially support a startup.

That’s exactly what our guest today focuses on – finding people that he knows he could trust and that are willing to go the extra mile for their business. Jeff Vinik is a man wearing many hats and throughout his professional career, he’s managed to switch from being a successful Wall Street investor to then being a hedge fund guy, to joining the real estate industry, to owning a sports team – the Tampa Bay Lightning – and on top of that, to being an early-stage tech investor.

Being in Jeff’s shoes is not an easy ride, and it takes a certain discipline in doing your due diligence and learning as much as you can about the industry you’re in or you’re thinking of joining. Today, we discuss his professional journey, why he wanted to switch gears and be part of multiple areas, as well as the types of people that he aims at surrounding himself with.

If you’re curious to learn more about Jeff and his early-stage investing, then tune in, and enjoy the show!

Some questions I ask:

How did you go from hedge fund to real estate? (02:19)
How has COVID affected your business? (07:42)
How did you get into early-stage technology investing? (12:20)
Do you have any stories there about a deal that you invested in that you’d never do again? (16:34)
What do you look for in founders? (17:44)
What do you do in your spare time? (29:38)

In this episode, you will learn:

The role Bill Gates plays in Jeff’s real estate ventures. (06:35)
Jeff’s thoughts on how the Tampa Bay area is going to evolve post-COVID. (04:40)
The four Ds of angel investing. (15:29)
Jeff’s experience with investing in eSports. (21:11)
The story of Embarc Collective. (24:37)

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Ryan Nece - Bucking the Trend Jun 19, 2020

Show notes

Ryan Nece’s journey to becoming a venture capitalist is unlike any we’ve ever seen. As a former NFL linebacker, Ryan defied the odds to become successful after retiring from the professional sports world. Now, he is the Managing Partner at Next Play Capital, founder of the Ryan Nece Foundation, and co-founder at StraightCast Media.

Throughout this episode, Ryan shares how he bucked the trend, refusing to undergo extreme financial stress like many other retired athletes. Instead, he treats business like a team sport, acknowledging that he’s only as good as those he surrounds himself with. Ryan breaks down what motivates him to pursue venture capital, how he evaluates the founders whom he invests in, and how he believes more founders from minority communities can get the funding they need to scale.

Some Questions I Ask:

How did you buck the trend of becoming financially stable after retiring from the NFL? (6:45)
What did your role look like with StraightCast Media? (14:40)
What do you look for in founders? (24:02)

In This Episode, You Will Learn:

How Ryan’s career led him to venture capital. (2:11)
What inspired Ryan to co-found his business StraightCast Media. (10:08)
Why Ryan decided to directly invest in Peloton early on. (21:05)
How Ryan evaluates the founders he wants to work with. (27:20)
How education and exposure will help founders from minority communities get the funding they need. (31:52)

Connect with Ryan Nece:

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

David Goldberg - Adjusting to the New Normal Jun 11, 2020

Show notes

David Goldberg’s trajectory into venture capital is a unique one. Directly after graduating from Law School and Business School, David worked as a criminal prosecutor, and eventually transitioned to global investment banking. During this time, he started his own men’s fashion company and sold it in 2013. This launched the rest of his career as an investor.

In this episode, David shares his journey to becoming a successful investor over the last 6 years, including his biggest mistakes and success stories. Furthermore, he discusses how the global COVID-19 pandemic affects his current investments, and what he believes the “new normal” will be like after the pandemic.

So get ready to hear more about David’s success story and learn about new and unique investment opportunities in the market now.

Some Questions I Ask:

What kind of investing do you do? (2:49)
What do you look for in a founder? (6:03)
What’s your big miss? (14:39)
What opportunities do you see presenting themselves as we transition into this “new normal”? (16:57)
What investment are you most excited about? (22:43)
What advice do you have for other investors? (25:48)

In This Episode, You Will Learn:

How David got to where he is today. (1:19)
David’s strategy for investing in technology: focus on companies reshaping the world. (2:56)
The process of David’s decision to invest in a deal with an outdoor gear rental company. (6:59)
How the COVID-19 pandemic affects investments. (10:38)
Why pet food companies are great investment opportunities. (15:26)
What the future of valuations looks like. (20:50)
What drew David to his first investment. (24:13)

More about Florida Funders:

Website

Our Investment Process

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Peter Mallouk - 5 Mistakes Every Investor Makes Apr 29, 2020

Show notes

Peter Mallouk is a little different than most investors interviewed on this podcast. Peter isn’t really an angel investor, but he is qualified as an investor. Peter is the President of Creative Planning, which provides wealth management services to clients. They manage roughly $48 billion among clients throughout all 50 states.

In this episode, Peter shares insights into how he became an investor, how he handles his clients’ wealth, what role the timing of markets plays in his strategy. He also shares some knowledge from his book, The Five Mistakes Every Investor Makes, including what big behavioral mistakes investors should avoid.

So get ready to see investing in a new light and discover strategies to grow your wealth.

Some Questions I Ask:

Tell us about your background and your firm. (1:40)
What drew you to the world of investing? (3:22)
What’s your approach to investing and growing your clients’ wealth? (4:30)
How do you look at the timing of markets? (11:21)
When you look at the dry powder from private equity, what does that mean for investors going forward? (26:00)

In This Episode, You Will Learn:

How Peter transitioned from an advisor to investor. (3:26)
How Peter customizes investment plans for his clients. (4:40)
What big behavioral mistakes investors tend to make. (6:24)
Why Peter avoids getting involved in venture capital. (16:28)
Why people choose private equity investments over public markets. (26:28)

Resources:

The Five Mistakes Every Investor Makes by Peter Mallouk

Creative Planning

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Chris Sullivan - The Future of the Restaurant Industry Apr 15, 2020

Show notes

Chris Sullivan has always been passionate about the restaurant business—starting from the time bartending and waiting tables. Chris co-founded Outback Steakhouse, which started as a one-story restaurant in Tampa, FL and has now over a thousand locations in 23 separate countries.

In this episode, Chris shares his story and every step he took to find the success he has today. He goes further to share advice for other founders, how his vision for business shifted to focusing on angel investing, and how he became Entrepreneur of the Year.

So get ready to learn Chris’s success story and how he sees the future of the restaurant business.

Some Questions I Ask:

How did Outback Steakhouse come about? How did you get started? (0:56)
Where did the Australian theme for your restaurant come from? (5:28)
What did you learn throughout your journey that other founders should know? (10:03)
When did you start angel investing? (15:46)
When looking at angel investing, how much emphasis do you put on a jockey? (24:53)
From a technology standpoint, what do you think is the biggest impact we’re going to see in the restaurant industry in the next 5 years? (29:42)

In This Episode, You Will Learn:

How Chris’s vision for his business continuously developed over time. (7:36)
What makes business a team sport. (10:14)
How Chris was awarded Entrepreneur of the Year. (11:55)
How delivery technology is changing the restaurant experience. (27:43)

More about Florida Funders:

Website

Our Investment Process

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

Scott Gorlick - The Future of Investing Feb 04, 2020

Show notes

Scott Gorlick is a native of southern Florida, where he also became one of the first 100 employees to work at Uber. After working at Uber for 6 years, launching their platforms, and scaling their operations globally, he moved to the east coast to spend time investing and advising great startups.

In this episode, Scott shares some of the insights and lessons he learned as part of the team at Uber, and what his transition to angel investing was like. He explains a few of his top lessons learned from his investment experiences so far, including why he enjoys working with founders in groundbreaking situations.

So get ready to learn about what the future of investing in technology looks like.

Some Questions I Ask:

What lessons did you learn at Uber? (3:38)
How did you get started in angel investing? (8:52)
How do you get involved with the companies you invest in? (10:36)
What area of technology are you focusing on? (18:43)

In This Episode, You Will Learn:

What the evolution of Uber looked like. (3:06)
Why Uber’s IPO is changing drastically & what to expect in the future. (7:19)
What Scott’s learned from angel investing. (9:02)
How valuations differ outside of Florida. (12:35)
Why Scott enjoys working directly with founders. (16:43)

More about Florida Funders:

Website

Our Investment Process

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

Steve MacDonald - The Art and Science of Angel Investing Jan 21, 2020

Show notes

Angel investing is part art, part science.

Oftentimes you trust your gut when deciding to put your finances, effort, and time into a company. In the early stages, you partner up with friends and family, and you choose your investments based on whether you like those people or not. But, as you move further down the spectrum, it becomes more science.

In today’s episode, Steve and I discuss how to choose the companies you want to financially support, and also, some of the red flags for angel investing.

Steven MacDonald is a serial entrepreneur who founded, among others, TechHealth and myMatrixx – the first web-enabled pharmacy benefits manager. The successful experiences in the entrepreneurial world led Steve into angel investing and now he is a Partner and a Board Member at Florida Funders and he helps find, fund, and build the next generation of technology companies in Florida.

So, listen to Episode 06, to learn, from an expert in the field, what are the rewards of angel investing and how you can actively be involved in the companies you want to support.

Questions I ask:

While you were building myMatrixx, what were some of the things that you learned, lessons learned as an entrepreneur, that maybe even help you as an angel investor today? (04:00)
When and how did you start angel investing? (05:31)
What do you look for in a founder? What is it that excites you? And why you want to invest in this founder and not that founder? And is the founder the most important thing? (11:38)
What are some of the things that you, as a board member and investor, can help a company with? (17:05)
What differences do you see between the startup community and investing in Silicon Valley, San Francisco versus Florida? (20:45)

In this episode, you will learn:

Steve’s background in the business world. (01:54)
The reasons angel investing is viewed as part art, part science. (06:03)
What to look for, when considering to invest in a company. (10:27)
Our processing power and Moore’s law – the two essential components that spin the wheel of technology advancement. (14:46)
Steve’s favorite companies that he has invested in. (20:00)

Connect with Steve:

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

Alexis Ohanian - Investing in Tech Startups Jan 07, 2020

Show notes

Currently, Miami is mostly seen as a town to party in or a town for so many other industries that are not tech. These perceptions are about to change, as more talented people are turning their attention to this delightful place.

On today’s episode, I am joined by Alexis - one of the co-founders of Reddit, who is an important player in the angel investing area, and Andrew – the founder of Papa, a Florida-based company. Alexis invested in Andrew’s business, and they are sharing with us their entrepreneurial journey.

Alexis Ohanian co-founded Initialized Capital with Garry Tan, in 2012. Alexis's expertise includes product, marketing, and community, and he is a prolific early-stage investor. Alexis was a co-founder of Reddit, the third-largest website in the US, which was funded by Y Combinator in 2005 and acquired by Condé Nast in 2006. He also served as a partner at Y Combinator and wrote the bestselling book Without Their Permission.

Andrew Parker is the founder and CEO of Papa – a Florida-based tech startup. He started the company to support a personal need with his grandfather. Papa provides on-demand personal assistance and socialization to seniors.

So, listen to Episode 05, to learn about the future of Florida, tech-wise, and what we can do to attract more people to start their business here.

Questions I ask:

How did you guys meet? (07:51)
Andrew, I saw you expanded geographically. Tell us about that. (11:52)
Alexis, what do you think of the deal flow here in investments versus California? (12:39)
What tech do you see coming down the road, in terms of technology, from an investment standpoint? (16:33)
Have you had any issues with recruiting people you need? (20:43)

In this episode, you will learn:

How Initialized was born. (02:32)
How Papa became a business. (04:21)
Alexis’s experience with Y Combinator. (05:26)
The reasons why technology can never replace the human touch. (18:08)
What Florida needs to do right now, to become an important player in the tech space. (21:22)

Connect with Alexis:

Connect with Andrew:

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