Skin in the Game VC Podcast

Latest Episodes:

Reuben Pressman - Your Passion Makes a Difference Oct 05, 2021

Show notes

Have you ever had a moment of recognition that an issue you were experiencing was readily solvable, and you might just be the one to figure out how?

Reuben Pressman started on the journey that brought him to where he is today when he began coding as a 10-year-old. As a student at the University of South Florida, he realized that the majority of the learning he was doing was going on outside the classroom—and that student involvement was a huge blind spot at his and many other schools.

After this a-ha moment as a student, Pressman set out to make it easy to collect usable data, then give the tools that institutions needed to make an impact. Launched in May of 2014, his company Presence has spent the last seven years doing just that.

Pressman is the founder and has served as CEO of Presence for more than nine years. The software serves to help universities improve retention rates by tracking data related to student involvement patterns and behaviors. In addition, he was recently announced as the CPO at Modern Campus, a higher education software company. He also serves as Entrepreneur in Residence for the city of St Petersburg, Florida.

Find out why Pressman believes the most important trait in an employee is their ability to be a team player and the fortuitous way he first connected with Tom, in today’s episode of Investing in Florida Technology.

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Some Questions Asked:

What can you tell us about Presence and the journey that brought you here? (03:08)
Who was your first customer? (05:17)
Where was the tipping point when you realized you would be able to scale and grow the company? (08:20)
Tell us about your time as the Entrepreneur in Residence for the city of St Pete. (12:50)
What made you decide that it might be time to sell? (17:54)

In this episode, you will learn:

How Presence and its mission grew out of Pressman’s observations about his own college experience. (03:20)
How Pressman worked through all of the bureaucracy involved in selling to universities. (06:42)
The fundraising journey behind Presence. (09:45)
Pressman’s advice for founders who are just starting out right now. (14:47)
Where Pressman sees himself going after Presence. (21:02)

Connect with Reuben:

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Manny Medina - Master of Reinvention Sep 14, 2021

Show notes

Have you ever wondered what it takes for a young immigrant to truly achieve the American dream? Well, you might just be able to learn a thing or two from Manny Medina’s story.

After emigrating to Miami as a young teen and—as he puts it—surviving high school, Medina was able to develop a unique and valuable perspective on the US-Latin American market. From his jetsetting early years as a CPA at PricewaterhouseCoopers, to his time in Kuwait helping rebuild after the liberation, to creating network access points while the internet was still in its infancy, Medina has frequently been at the center of some of the most important industry events of the last 50 years.

Medina’s decision in the late 1980s to take the leap of faith from real estate to tech when he found himself at a crossroads might’ve been the most important move he ever made. He was able to reinvent himself and his company, Terremark, once again, from a highly successful developer to an early adopter of burgeoning internet tech, where he found his true calling.

Medina served as Chairman of the Board, President, and Chief Executive Officer of Terremark until 2011, when the company was acquired by Verizon Communications. In 2012, he founded Medina Capital, a private equity firm with a focus on emerging cybersecurity technologies where he currently serves as managing partner. He is also the founder and chairman of eMerge Americas, a tech networking event that serves to connect the US, Latin America, and Europe.

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Some Questions Asked:

What made you decide to take the risk of leaving your job at Pricewaterhouse to become an entrepreneur? (05:13)
How long did you have your first firm? (7:23)
What was the turning point where you realized your company would survive the dot com bubble bursting? (14:49)
How much change has there been since you started in the ability to recruit for tech positions within Florida? (20:31)
What's Medina capital working on now? (23:21)

In this episode, you will learn:

About Medina’s experience immigrating to the US from Cuba at 13. (02:25)
How the real estate crash of the late ’80s spurred Medina’s move to tech. (08:07)
The origin story of Terremark Worldwide. (09:51)
The one surprising thing Medina did after Terremark was sold that he had never allowed himself to do before. (16:28)
Where Medina sees Miami’s tech industry going in the next 5-10 years. (26:26)

Connect with Manny:

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Claudia Duran - Taking Start-Ups to the Next Level Sep 01, 2021

Show notes

The world of entrepreneurship is more harrowing, thrilling, and rewarding as ever, but the past year and a half has been especially exciting for Florida investors. With the influx of people from New York, California, and even from Latin America, the area has experienced an incredible boom that has benefited investors and entrepreneurs alike. One such industry growing exponentially from all of this? Organizations that are designed to incubate entrepreneurs like Endeavor, where Claudia Duran serves as the managing director.

Claudia works with Endeavor Miami, a global organization in over 30 markets, to identify high-impact entrepreneurs—those who have big ideas and are taking their ideas to the next step. Endeavor then works with those entrepreneurs to accelerate their growth by creating connections with mentors and investors.

We talk about what Endeavor is doing to encourage and stimulate start-ups, and Claudia takes me through her personal history, from her roots in El Salvador to her time as a finance major at Penn State. Claudia also tells me what it takes for a company to be selected by Endeavor, what their mentorship program looks like, and how once you’re an Endeavor entrepreneur, you’re part of that global network for life.

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Some Questions Asked:

Can you tell us a little about Endeavor Miami’s mission? (02:47)
How did you get from El Salvador to the United States? (04:46)
What are you looking for in these companies you choose to take into a cohort? And what does that process look like? (07:21)
How many companies will apply for you to get to your 10? And what are you looking for in those 10 companies that you end up choosing? (12:02)
How many companies have you seen go through your program since you’ve been in Miami?
Are there any portfolio companies you want to highlight? That you're very excited about? (20:42)

In this episode, you will learn:

A bit about Claudia’s personal background (03:51)
What the cohort experience looks like for companies that are selected by Endeavor (09:41)
How some companies end up pivoting their business model as a result of their time with Endeavor (13:44)
What happens with the entrepreneurs after Endeavor’s mentorship is over (16:54)
Why Florida is the site of the next big tech ecosystem (26:54)

Connect with Claudia:

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Rennick Palley - Crypto Crash Course Jun 16, 2021

Show notes

To the traditional investor, the world of cryptocurrency can be intimidating. Luckily, my guest today is an expert in the field and helps us break it all down. If you’ve found yourself wondering about crypto, DeFi, and the blockchain economy, listen in—you may discover this brave new world of finance isn’t quite as complicated as you might think.

Join me today as I welcome Rennick Palley, founder and CIO at Stratos Technologies. Rennick is an MIT graduate who started his career on Wall Street before turning his interest toward financial technology. He is also a co-founder of Goldfinch Finance, a decentralized global bank that aims to change the face of investing in businesses.

We unravel the differences between Bitcoin and Ethereum, the relevancy of blockchain supply and demand, and how we may be looking at a not-so-distant future in which only a few of these new currencies remain relevant. Rennick also expands on the implications of blockchain in regards to global finance, and what that could mean for business finance over the world.

Find out how Rennick went from Wall Street to venture capital projects, and how the professional mentoring he gained at a global equity fund helped him get there. Learn why Rennick believes that productivity is driven by technological advances, his view on the pitfalls of consumer banking in the US, and what led him to the world of blockchain and crypto.

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Some Questions Asked:

How did you end up at MIT? (4:08)
What took you from Wall Street to the world of crypto? (5:56)
How would you compare Bitcoin to Ethereum? (10:09)
Do you think that we’ll eventually only have a few different cryptocurrencies? (14:06)
What is China’s place in all of this? (25:14)
What can you tell us about Goldfinch Finance? (29:09)

In this episode, you will learn:

A bit about Rennick’s professional background (2:14)
How Rennick’s beliefs about investment strategy changed over time (4:44)
About Rennick’s professional mentor (6:01)
The difference between crypto, DeFi, and blockchain (16:20)
The implications of a liquid form of currency on the global economy (25:13)
The key differences between angel investing and the Goldfinch blockchain system (33:33)

Connect with Rennick:

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Brian Butler - From Army Officer to CEO Mar 16, 2021

Show notes

Curious as to how military training prepares you for the world of entrepreneurship?

If you’ve ever found yourself at a crossroads in your career and felt that you just aren’t being offered anything to your liking, have you ever thought of striking out on your own? Entrepreneurship is a complicated and humbling experience, but it also allows you to be your own boss and create the business you’ve always wanted to work for.

What happens when a former Army officer and member of the White House Homeland Security board retires from the military and decides to make his own luck? You get Brian Butler, founder and CEO of Vistra Communications. From college ROTC to working at the Pentagon to founding his own startup, Brain has experienced firsthand a remarkable professional career.

Vistra Communications handles PR, marketing, and consulting for a number of government and corporate contracts, including AT&T and Coca-Cola. Founded in 2007, they now employ over 100 people and have offices in both Florida and Northern Virginia.

As a 22 year veteran of the US Army, Brian has learned invaluable lessons through his service. Listen and learn what Brian attributes his success to and what we can do to help diversify the growing field of Florida entrepreneurs.

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Some Questions Asked:

How did you transition from the army to entrepreneurship? (4:33)
How did the military prepare you for the rollercoaster of business ownership? (7:22)
What did the army teach you about leadership? (8:50)
How can we fix the disparity in diversity amongst entrepreneurs? (14:58)
What impact does technology have on your business? (19:16)
Where does the military stand on adopting and developing technology? (21:22)

In this episode, you will learn:

How Brian got started as an entrepreneur. (2:27)
Why Brian believes that veterans make excellent employees. (6:05)
The type of attitude that makes a successful business leader. (11:15)
About the emerging start-up scene out of South Florida. (18:24)
Advice Brian has for founders. (25:13)

Connect with Brian:

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Steve Raymund - The Keys to Longevity Mar 02, 2021

Show notes

Have you ever wondered what it takes to develop true staying power in an industry as quick and variable as tech?

If you’re serious about making it in the tech world, there are certain attributes that will set you apart from the pack. Curiosity, humility, and the ability to see patterns are invaluable for anyone, but are absolute prerequisites for successful entrepreneurs. Couple these with a shrewd eye for team building and a knack for playing to your own strengths, and you may be well on your way to success.

When you hear names like Bill Gates and Mark Zuckerberg, the first thing that comes to mind will, of course, be that they’re titans in the tech industry. What might not immediately strike you is that they both built their empires from the ground up. Steve Raymund is one of the few others who also own that claim to fame. From his beginnings at the dawn of the 1980s tech boom to his diverse stable of investments today, Steve has managed to remain at the top of his game throughout the last 40 years.

Steve Raymund is the former CEO, co-founder, and board member of Tech Data, an IT products and services company headquartered in Clearwater, Florida. Steve led the company through early turmoil and self-described “rock bottom” during a nearly complete employee turnover, to going public a mere six years later, with $1 billion in annual sales by 1993.

Steve also serves as a board member for Jabil Inc, a $19 billion technology manufacturing company that provides parts to Apple and Microsoft.

As a 20-year CEO, Steve has learned some invaluable lessons. Find out why Paul touts Steve as a different kind of tech executive and the traits and personality type that Steve attributes much of his success to.

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Some Questions Asked:

To what do you attribute Tech Data’s longevity? (12:57)
What have you learned about managing people and creating a team? (17:30)
Is there one accomplishment in your career that stands out, that you're most proud of? (19:29)

In this episode, you will learn:

Steve’s experience as an early player in tech. (00:56)
What the rapidly growing tech marketplace, starting in the early '80s, looked like. (02:26)
The unique qualities that make up a different kind of tech leader. (7:11)
What to really look for in an angel investment opportunity. (25:48)
The key to making it all look so easy (and why the pain along the way is worth it!) (30:09)

Connect with Steve:

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Tom Wallace - The 5 Ds of Angel Investing Feb 16, 2021

Show notes

Being a successful angel investor requires a lot of work and commitment. At Florida Funders, our goal is to make it easier for people and increase their chances of finding the right opportunities for them. Being in this arena for over 25 years, we’ve learned valuable lessons on how to maximize the probability of great returns, and we’ve compiled these best practices into what we call “The 5 Ds of Angel Investing.”

In this episode, Tom Wallace talks in detail about these five important elements that every investor should pay attention to and rigorously follow whenever the opportunity to invest comes their way.

Tune in, and learn more about the 5 Ds of Angel Investing, and how Florida Funders can help both investors and founders to reach higher grounds in their ventures.

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In this episode, you will learn:

The 5 Ds of Angel Investing and why they are crucial for a successful angel investor. (00:45)
The importance of being selective about the companies you’re investing in (01:45)
The two parts of the due diligence process required for a great investment. (02:46)
The role played by domain expertise in having successful investments. (08:32)
The reason we encourage our investors to build a diversified portfolio. (09:52)
Why discipline plays a crucial part in angel investing. (11:14)
Why Florida Funders is making angel investing easy. (12:46)

Connect with Tom Wallace:

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Tom Wallace - The Journey to Florida Funders Feb 02, 2021

Show notes

At Florida Funders, we are helping early-stage companies get access to capital from investors through an online process and crowdfunding. We’re all about learning best practices and getting better at angel investing, and the purpose of this podcast is to interview some of the best and brightest and most successful investors and entrepreneurs to learn from them and get better in the process.

After interviewing a handful of people on the show and finding out what makes them tick, what motivates them, how they’ve built successful companies, and how they help others do the same, we thought it’s time to give you some background on Florida Funders – what sparked the idea and why it’s a great network for founders and funders.

Our host and Managing Partner, Tom Wallace, shares his journey in the angel investing world, as well as what drove him and his partners to start Florida Funders. Tom has learned the hard way how challenging angel and early-stage investing can be, and he has dedicated his life to making this process easier.

Tune in to learn more!

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In this episode, you will learn:

What brought Tom to Florida almost 30 years ago. (00:45)
The current Florida tech ecosystem. (02:28)
The venture that inspired Tom to dedicate full-time to angel investing. (04:01)
What Florida Funders offers to investors. (08:15)
The benefits of Florida Funders’ angel network. (09:58)

Connect with Tom and Florida Funders:

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Ashley Jarocki & Stephanie Markese - The Future of Hiring Jan 19, 2021

Show notes

What started as a friendship between two women cheerleading for the Buccaneers ended up in Next Path: a growing company providing hiring solutions for companies that see people as their competitive advantage.

In today's episode, Ashley Jarocki and Stephanie Markese share with us how they went from cheering on the same line together to making a leap of faith and starting their own company in the staffing world.

Stephanie Markese always wanted to be a dentist until she realized that she wanted something more than work for a salary for the rest or her life, where she could evolve and make her earnings grow. After a taste of staffing and sales, there was no coming back into dentistry.

Ashley Jarocki was looking for a change after five years in the corporate world. One day, she received a call from Stephanie proposing a leap of faith: bring your knowledge of the corporate world and let's start a company together.

Listen to the full episode, learn about the best way of dealing with the hiring process, how our guests think the staffing world will look like in the coming years, and how AI will deal with culture fit when filtering candidates for hire.

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Questions I ask:

Did you guys go into staffing together? (4:11)
Your industry changed a lot in the last year. How did COVID affect your business? (7:30 )
Any advice for entrepreneurs buildings their team? Should they do it themselves or hire a staffing firm? (10:13)
Is it possible to evaluate a candidate in a one-hour interview? (14:28)
How do you see things like 5G, AI, augmented reality, and other new technologies affecting your industry? (17:51)

In this episode, you will learn:

How Next Path was born (4:18)
Recruiting and staffing evolving with technology (7:30)
The reason why companies should look for culture fit when hiring (11:06)
AI or a person, who is better for culture fit? (20:56)
Are resumes still relevant in the LinkedIn era? (22:29)

Connect with Ashley Jarocki:

Instagram

Facebook

Connect with Stephanie Markese:

Instagram

Facebook

Next Path Resources:

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Paul Holland - The Precursors of Success Jan 05, 2021

Show notes

When you hear about a new idea, how can you be sure it’s good or bad?

As an investor, you have to be a calculated risk-taker. Of course, there’s the due diligence that can help you decide whether the business that’s presented to you is worth funding, but you still need a dose of courage to financially support an idea

Netflix is one of those successful businesses that weren’t short of ups and downs – and in this episode, you will hear the story of Netflix seen through the lens of one of the early investors: Paul Holland. Why did he choose to invest? What’s the background between Paul and Reed Hastings? And how did Netflix become one of the clear winners of the streaming wars? Tom and Paul also discuss the important role Paul’s new firm, Mach49 plays in helping global businesses drive meaningful growth to beat the startups at their own game.

Paul Holland is Managing Director and VC-in-Residence at Mach49, where he leads the company’s Corporate Venture Investing Practice. Paul works with global businesses to design, launch, and manage corporate venture funds that leverage the experience, deal flow, global network, and success of his top-tier Silicon Valley VCs.

Prior to joining Mach49, he was a General Partner for 18 years at leading venture capital fund Foundation Capital, helping take startup companies from zero to $100M, to IPO, or acquisition. His amazing background also includes partnering with Reed Hastings at Pure Software and joining Mark Gainey at Kana Communications.

Paul enjoys being on the front lines, working side by side with entrepreneurs developing fast-growing, dynamic new ventures. His investing stories are diverse and interesting, so tune in and find out how he met Reed Hastings and invested in Netflix, how he supported Chegg, as well as what Mach49 is all about.

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Some questions asked: