Skin in the Game VC Podcast

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Latest Episodes:

Dave Sachse: Redefining Venture with Family Offices Oct 30, 2024

Dave Sachse is the founder of Family VC and a leader in the world of family office investing, where he helps family offices navigate venture capital by building networks, sharing resources, and creating opportunities for collaboration. With a background in managing his own family's single-family office in Wisconsin, Dave has a deep understanding of the unique challenges family offices face when investing in early-stage tech companies. He founded Family VC to connect like-minded family offices, fostering a community of over 200 members who share deal flow, best practices, and strategic insights in venture capital.

Dave is passionate about tech innovation and values-aligned investing, favoring pre-seed to Series A stages where family offices can add real value beyond funding. His approach is hands-on and collaborative, leveraging partnerships with experienced VCs and investing in diverse tech sectors across the U.S. Family VC aims to make family offices a lasting force in the venture world, helping these investors move beyond traditional asset classes to become impactful players in early-stage tech.

Tune into this episode of Skin in the Game VC to hear more of Dave’s insights on the shifting landscape of venture capital and the role family offices are playing in supporting the next generation of innovation.

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Jeff Gigante: More Than a Meal – The Rise of Experiential Dining Oct 17, 2024

In the latest episode of the Skin in the Game VC podcast, hosts Tom Wallace and Saxon Baum sit down with Jeff Gigante, co-founder of Next Level Brands and a major player in Tampa’s restaurant scene. This conversation dives deep into Jeff’s entrepreneurial journey, starting with his first pizzeria at Florida State to now running some of the hottest restaurants in Florida.

Jeff shares how his passion for creating unique dining experiences has shaped his career, and he’s candid about the challenges along the way—whether it was opening his first restaurant with a phone tutorial from Italy or navigating the complexities of growing a business during the pandemic.

What’s really exciting is how Jeff, Tom and Saxon explore the impact of technology on the restaurant industry. From AI answering systems to cloud-based POS systems and even robotics, it's clear that tech is revolutionizing how restaurants operate. Yet, Jeff reminds us that hospitality is still about human connection, something he believes will always be central to full-service dining.

If you’re into startups, tech innovation, or just curious about what it takes to succeed as an entrepreneur, this episode is packed with insights. Plus, it’s always inspiring to hear from someone like Jeff, who not only talks about success but also how important it is to care for your investors and build lasting relationships.

This is a great listen for anyone looking to learn from someone who’s been through it all and come out stronger on the other side.

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General Tony Thomas: Beyond the Uniform Sep 16, 2024

Ever wondered how a military leader transitions to the world of venture capital? In our latest episode of Skin in the Game, we sat down with retired Four-Star General Tony Thomas to discuss his incredible journey. From leading special operations forces to investing in cutting-edge technologies, General Thomas shares his unique insights on leadership, innovation, and the intersection of the military and the private sector. Listen now to hear about his experiences, his thoughts on dual-purpose technology, and his perspective on the world stage

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Patrick Murphy: Estimating the Future of AI & Construction Aug 30, 2024

In this podcast episode, we delve into the world of AI and its transformative potential for the construction industry. Our guest, Patrick Murphy, a former U.S. Congressman and construction industry veteran, shares insights on his company Togalai, which utilizes AI to automate the estimating process in construction.

Murphy discusses the challenges and opportunities presented by AI, emphasizing the importance of data and domain-specific expertise. He also addresses the ethical and legal implications of AI in construction, highlighting the potential for both job creation and displacement.

The conversation extends to explore the applications of 3D printing and sustainable building materials like RENCO. Murphy outlines Togalai's future goals, including global expansion and the development of new AI features.

Overall, this episode provides a valuable perspective on the future of AI in construction, its potential benefits, and the challenges that lie ahead. Tune in to hear the whole episode.

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Mayor Jane Castor: Tampa's Rise as a Tech Hub Jul 08, 2024

Join us for an insightful episode of the Skin in the Game VC Podcast with Tampa Mayor Jane Castor, discussing the city's thriving tech ecosystem, strategic growth during COVID, and the role of AI in governance. Mayor Castor highlights Tampa's appeal as a tech hub, the importance of organic growth in the tech scene, and the city's focus on talent and innovation. Tune in to learn how Tampa is positioning itself for continued success in the tech industry!

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Beyond Bitcoin: Unveiling the Future of Finance with Zaid Rahman Jun 27, 2024

The episode features Zaid Rahman, CEO of Flex, a Florida Funders portfolio company. Zaid discusses his entrepreneurial journey, Flex's rapid growth in providing financial services to small and medium businesses, and their expansion plans. He shares insights on talent acquisition, customer marketing, and creating a comprehensive financial platform for mid-market businesses.

In a rapid-fire Q&A, Zaid offers his optimistic outlook on the future, predicting AI as a job creator, Bitcoin's rise, Tesla's dominance in transportation, Miami becoming a major tech hub, and even Jake Paul's victory in his upcoming fight against Mike Tyson.

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Frank Smith: From YouTube to Multimedia Mogul Apr 30, 2024

Discover the fascinating journey of Frank Smith, from YouTube sensation to Multimedia Mogul, in the latest episode of the Skin in the Game pod. Join Saxon Baum as he dives into a captivating conversation with Frank, tracing his evolution and success in the multimedia landscape. From crafting short-form sports videos on TikTok to navigating the complexities of influencer marketing trends, Frank shares invaluable insights and strategies. Explore the rise of personal brands in sports media and the future of content consumption with Frank's astute observations. Witness the emergence of Frank Smith as a trailblazer, pushing the boundaries of creativity and engagement in the digital age. Don't miss out on Frank's revolutionary projects and follow him across platforms to stay updated on his groundbreaking work.

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Charmel Maynard: Creating a Legacy in Finance Apr 08, 2024

Tune in to the latest episode of the Skin in the Game VC Podcast featuring Charmel Maynard, Chief Investment Officer of the University of Miami. Gain invaluable insights into university asset management and the journey that led Charmel to his prestigious position. Discover the strategies and decisions driving investments, and learn about the dynamic nature of his role overseeing three distinct pools of capital. Whether you're a seasoned pro or just curious about finance, this episode offers valuable perspectives on responsible asset stewardship. Don't miss out on Charmel's wisdom and expertise!

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Delian Asparouhov: From Bulgaria to Silicon Valley Mar 27, 2024

Delian Asparouhov, a Bulgarian-born, self-made software engineer, dives into the rollercoaster of a journey from being an MIT dropout to earning the Thiel Fellowship. Delian discusses his initial reservations about a career in venture capital and how early exposure to the field via an internship at Square, a student-run VC, helped change his mind and led him closer to his purpose. Delian touches on how he accidentally fell into a full-time venture capital role and how, over time, his skepticism ignited into a passion. Delian also covers his experience as a partner at Founders Fund.

This episode explores recent pullbacks in the crypto market – and what these changes spell out for investors – but also gets into the space-born industry and Varda, a first-of-its-kind orbital manufacturing platform, where Delian serves as co-founder. Tune in to hear Tom Wallace and Saxon Baum on Skin in the Game.

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Lucy Guo: Passes & Perspectives Jan 29, 2024

In this podcast episode, Lucy Guo, a prominent entrepreneur and Thiel Fellow, shares her remarkable journey from receiving a Thiel Fellowship at the age of 20 to becoming the second wealthiest self-made female in the United States. Lucy discusses her experiences with ventures such as Scale AI, her transition from venture capitalist to entrepreneur, and the evolution of her venture fund, HF0.

The conversation explores Lucy's latest venture, Passes, a platform for content creators, where she emphasizes the importance of investing in engineers and discusses the role of AI in the creator economy. Lucy reflects on her move to Miami, highlighting the differences in the tech landscape and the need for increased capital in the ecosystem. Listen to find out more.

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Steve MacDonald: International Tech Trails & Tales Nov 16, 2023

This episode focuses on Steve MacDonald’s unique experience of spending a year in Florence, Italy, while exploring the cultural and historical aspects, as well as insights into the local tech scene.

Steve shares that the decision to move to Florence was driven by a long-standing desire to experience life abroad with his family. He reflects on the cultural differences, the historical richness of Florence, and the challenges of adapting to a different lifestyle. Steve also highlights his travels within Europe during this period.

The podcast delves into the tech scene in Italy as well a noting cultural nuances affecting entrepreneurship. In contrast to the U.S., failure is not culturally acceptable in Italy, making it a challenge for startups. Additionally, Steve provides insights into the venture capital landscape in Europe, noting the conservative approach and a lack of angel investors.

Upon returning to the U.S., Steve shares his observations on the current market environment, emphasizing the prolonged timeline for startup exits and the impact of changing economic conditions on valuations. He stresses the importance for startups to focus on profitability and cash preservation.

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David Goldberg: Navigating the Evolving Tech Landscape Nov 07, 2023

In this particular episode, Tom and Saxon touch on various subjects, such as the bankruptcy of WeWork, the impact of EVs on traditional automakers, and the changing landscape of commercial real estate due to remote work trends. Guest speaker, David Goldberg, a partner at Alpaca Ventures, talks about his background, the branding of Alpaca Ventures, and their approach to venture capital.

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Joe Bayen: Journey From Success to Failure and Back Oct 26, 2023

Joe Bayen, who was Born in Cameroon, shares his journey of moving to the United States as a three-year-old and being raised in Paris, France. Joe shares his experience in the credit industry, starting with his realization of the impact of late payments on his credit score. This led him to found a company aimed at helping students manage their credit.

Joe worked on the development of the Bootstrap app, which garnered millions of installs and revenue through a successful business model of offering free downloads of paid apps for a few days. However, the business model suffered when Apple changed the app store rules, resulting in a sudden loss of revenue.

Join Tom Wallace and Saxon Baum as Joe dives into what it looked like going from success to failure then back to success.

Link for the "State of Seed and Early Stage Investing Quarterly Update" by Saxon Baum: https://www.floridafunders.com/resources/blog/the-state-seed-early-stage-investing/

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Matthew & Michael Vega-Sanz: Finding Passion in the Ordinary Aug 03, 2023

Founders of Lula, Michael and Matthew Vega-Sanz joins the episode of Skin In The Game VC Podcast with Tom Wallace and new co-host Saxon Baum.

Matthew and Michael discuss their journey of creating a car sharing app called Lula. They talk about how they came up with the idea while in college and built an app that initially had many flaws. However, over time, the app gained traction and went viral, becoming one of the top car sharing apps in the country.

They also faced challenges in securing insurance coverage for their rentals but eventually found an insurance company to work with.

The two founders emphasize their passion for insurance and how it touches every aspect of life. The two brothers mention using data points to assess risk when users sign up for their service. Michael and Matthew mention a pivotal moment in which they decided to pivot from being a car rental company to focusing on insurance. Lula provides insurance-related services, including claims management and risk reduction. They help companies save money by reducing insurance expenses and optimizing teams.

Lula has experienced significant growth, increasing their customer base from 99 to nearly 4000 companies in just over a year.

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Laura DiBella: Florida's Tech Bloom Jun 01, 2023

Laura DiBella, the Secretary of Commerce for the State of Florida as well as the president of CEO of Enterprise Florida, joins us for this episode of Skin in the Game.

Laura explores the robust evolution of Florida's tech industry and the state's response to COVID-19. Florida's open strategy during the pandemic made the state a magnet for tech talents, thereby catalyzing innovation. She acknowledges the pivotal role of a diverse talent pool and universities in creating a vibrant business environment.

They shift focus to Enterprise Florida, a public-private partnership established in 1996, aimed at spurring economic growth. Despite its impending merger into the Department of Commerce, Laura counters misconceptions about its effectiveness, underlining its contributions, including the Florida Opportunity Fund, its venture capital arm. She points to its successful model as proof of its integral role in Florida's economic development.

Get an inside look at emerging technologies, with Laura unveiling Florida's ambition to be at the forefront of electric vehicle take-off and landing (eVTOL) technology. Florida's geographic characteristics and existing infrastructure make it an ideal location for the deployment of this technology,

As for the current political climate, Laura expresses hope for more unity and collaboration in government. She believes challenging economic times could forge a sense of unity, leading to a more stable, effective, and trusted government.

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Investing in Startups with Brad Feld Feb 01, 2023

Brad Feld, an avid ecosystem-builder, tech entrepreneur, and early-stage investor for over 35 years shares his insights on the venture capital, startup, and tech community in this episode of Skin in the Game VC Podcast. Brad began his journey in tech and venture capital in the ‘80s and has since become a respected and influential figure in the industry. He has written several books on entrepreneurship and venture capital and started blogging in 2004 before VC Twitter existed.

Join Tom Wallace as he dives into the world of angel investing in startups with Brad Feld where they’ll discuss his successes, what it takes, and where startup investing could be going.

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Building a Betr Company with Joe Levy Aug 12, 2022

On this episode, Tom interviews Joey Levy. You may have seen him recently all over the news and social media alongside his business partner and top sports influencer Jake Paul. They have recently launched Betr (initially known as Instabet), the world’s first micro-betting focused app and new media venture for the next generation of sports fans.

If you want to learn more about investing in early-stage tech like a venture capitalist, be sure to visit the Florida Funders website at floridafunders.com. Join our angel network at no cost and get access to Florida Funders VC-vetted investment opportunities in the next great breakout tech companies.

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Building a Tech Community with Lakshmi Shenoy of Embarc Collective Jul 13, 2022

Lakshmi Shenoy is the CEO of Embarc Collective in Tampa, Florida. Tom Wallace discusses her story and how she ended up helping to build and lead the fastest-growing startup hub in Florida.

If you like what you hear, please rate us 5 stars and check out other episodes here: https://www.floridafunders.com/category/podcast/

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Lessons Learned in Early Stage Tech Investing During Market Downturns Jul 13, 2022

Florida Funders partners Tom Wallace and Marc Blumenthal discuss the ups and downs of markets and the lessons learned from the past. Learn more about early-stage tech investing during these times.

If you like what you hear, please rate us 5 stars and check out our site: https://www.floridafunders.com/category/podcast/

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Tony DiBenedetto: Thinking Big Apr 28, 2022

Hello, my name's Tom Wallace, and I'm the Managing Partner of Florida Funders. Welcome to Florida Funders podcast. Our podcast is all about how to make all of us better angel investors, or better founders or entrepreneurs. We really address two audiences here. One thing that I love about angel investing and entrepreneurship is, it's so dynamic, so fluid, and there's always something new to learn, and somebody new to learn from. Our guest this week is Tony Dibenedetto.

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Elias Torres: Elevating Minority Founders Dec 14, 2021

When you paint a picture in your head of the American Dream, what do you see? For many of us, it involves the vision of being ‘self-made’ and designing our own destiny, no matter where we came from.

For Elias Torres, the choice his mother made when she immigrated from Nicaragua to Tampa would prove to be a fortuitous one in helping him realize that dream. After his early start at IBM, Torres became committed to the vision of entrepreneurship. With Drift, his current company, he has proven time and again that Latino founders deserve a place amongst the world’s biggest capital projects.

Torres is the founder and CTO of Drift, the world's leading conversational marketing and sales platform.Drift helps businesses connect with customers who are ready to buy. After just three years in the market, Drift has become one of the fastest growing SaaS companies of all-time and was named to the Forbes Cloud 100, LinkedIn Top 50 Startups, Entrepreneur's Top Company Cultures, Boston Business Journal's Best Places to Work, and SaaS Company of the Year by the NEVCA.

Listen to today’s episode of Investing in Florida Technology and hear how Elias made the incredible leap from struggling to take orders in English at his fast food job as a teen to becoming Chief Technology Officer of his own company. He also discusses dealing with imposter syndrome, starting with a new company just weeks before the 2008 crash, and the major expansion plans he has for Drift.

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Some Questions Asked:

You came here at a young age from another country, can you tell us about that? (01:37)
What was your first entrepreneurial venture? (12:32)
Can you tell us about Drift, your current company? (17:30)
Can you explain to the listeners the difference between venture capital and private equity? (31:29)
Would you ever consider moving Drift’s headquarters to Florida? (39:59)

In this episode, you will learn:

How and when Torres became interested in tech (03:48)
Torres’s early start with IBM (06:42)
What the original vision was for Drift (21:43)
Why venture capitalists love first generation immigrants (25:49)

Connect with Elias:

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David Blumberg: From the Bay to the Magic City Nov 30, 2021

It's been more than 18 months since the COVID-19 pandemic started and we experienced weeks of lockdowns, quarantines, and a total reconfiguration of the way we work.

For venture capitalist David Blumberg, the pandemic took him from his ancestral home of California across the country to Florida. Realizing that he was no longer chained to his fixed, physical office in San Francisco, he took the plunge and moved over 3,000 miles in order to take advantage of the up-and-coming vibe of Miami, as well as the state’s business-friendly regulations and taxes. David learned how to take advantage of the pandemic and was able to recognize it as -- as he puts it -- a catalyst of virtualization, innovation, and decentralization.

Blumberg is the founder and managing partner of Blumberg Capital, a private Venture Capital firm investing in early-stage IT, digital media, social media, mobility, Internet, e-commerce, payments, SaaS, and tech-enabled services. He also serves as a board member of Credorax, Trulioo, IntSights, and Slync.io. David holds an undergraduate degree from Harvard University and an MBA from Stanford University Graduate School of Business.

Listen to today’s episode of Investing in Florida Technology and find out how David made the leap from studying government to becoming a venture capitalist, how he embraces virtualization, and why he believes that the 21st century will be one of massive innovation and productivity for office and service work.

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Some Questions Asked:

Can you tell our audience a bit about your background and where you grew up? (01:54)
You have this tie with Israel, when did that start? (14:10)
What do you see in Florida and Miami? (22:41)
What are you looking for in a founder? (29:38)

In this episode, you will learn:

Why Miami made the top of David’s list when he and his family decided to relocate (03:16)
About taking ‘acorns’ and turning them into unicorns (09:41)
How patience has paid off for Blumberg Capital (12:57)
A little about the Israeli company that David and Tom are both investors in (20:01)
Venture capitalists either follow the NASCAR model or the marionette model (33:59)

Connect with David:

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Brian Murphy: the Importance of Reinvention Nov 16, 2021

What happens when a brand new tech startup finds itself in the middle of one of the worst financial crises the country has ever seen? With a little luck, some intuitiveness, and a lot of hard work, a pivot in the right direction can not only save a company, it can create major success, too.

Brian Murphy founded ReliaQuest in 2007, just as the US was plunging into the Great Recession. While he didn’t know it yet, a DoD contract would come to be instrumental in the company’s pivot from IT to cybersecurity. In the years following, Murphy was able again to lead the company with flexibility to a market that better suited them.

Murphy is the CEO and founder of ReliaQuest, a cybersecurity company serving enterprises globally. ReliaQuest, the leader in Open XDR-as-a-Service, is known for being the force multiplier for security operations teams. He also serves on the board of Embarc Collective, a Tampa Bay-area startup incubator, and is an official member of the Forbes Technology Council.

On today’s episode of Investing in Florida Technology, Murphy speaks about the evolution of ReliaQuest, his advice to founders that are just starting out, and how he still finds time to serve as a chairman on the board of Embarc Collective. He also discusses the big pivot that brought ReliaQuest to where it is today and what he sees happening in the industry looking ahead.

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Some Questions Asked:

Can you tell us a little about your background? (01:50)
How did you make the switch to recurring revenue? (06:20)
Have you had any trouble attracting talent in Florida? (08:47)
How did COVID affect ReliaQuest? (12:02)
Where is most of your hiring taking place? (14:06)
Are you being acquisitive? Or are you still just growing organically? (15:58)

In this episode, you will learn:

What inspired Murphy to start ReliaQuest (2:41)
A little about the software team at ReliaQuest (07:50)
About the growing cybersecurity industry in Tampa (10:57)
Brian's experience with bootstrapping (14:53)
Where Brian sees ReliaQuest going in the next 5-10 years (23:04)

Connect with Brian:

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Hugh Campbell - Entrepreneurship as a Team Sport Nov 02, 2021

Discipline, initiative, and responsibility are all skills you would expect a young person to learn in the military. But what about teamwork and learning to successfully collaborate with others as a whole greater than its parts? For Hugh Campbell, his time in the US Army taught him this invaluable lesson.

When Campbell entered West Point fresh out of high school, he never dreamed of the opportunities that would soon be accessible to him. Through his work as a communications officer, Campbell learned invaluable lessons about leadership, problem-solving, and tech. After leaving the military and joining the private sector, Campbell put to work the skills that he had honed, which led directly to his many successes and a career as an “accidental entrepreneur.”

Campbell currently serves as President of AC4S Technologies, a hybrid cloud solutions provider. Prior to his current position, he served as CEO of AC4S for 16 years. Before that, he held positions in planning, designing, and implementing large-scale telecommunications networks for companies like Intermedia Communications and Accelacom. He also serves as Chairman of the Board for the CEO Council of Tampa Bay and as a member of the board of trustees for BayCare Health System.

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Some Questions Asked:

Where did you grow up and how did you end up at West Point? (04:07)
Where did you go after you left the military? (07:10)
How did West Point and the military prepare you for being an entrepreneur? (11:21)
How can people like me invest more in minority founders? (18:25)

In this episode, you will learn:

About AC4S Technologies and where the name came from. (02:25)
How Campbell became what he calls an “accidental entrepreneur.” (08:21)
The advice Campbell has for young, hungry founders who are just starting out and why it’s so important to make sure you’re really vetting the partners you’re going into business with. (12:34)
Why being an entrepreneur isn’t for the faint of heart and easily discouraged—and why it’s best to play the game as a team sport. (15:22)

Connect with Hugh:

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Arnie Bellini - The Case for Being an Early Adopter Oct 19, 2021

We’ve all had that lightbulb moment at least once in our lives, where we have a striking realization seemingly independent of everyone else around us. What we don’t all have the privilege of experiencing? Having that moment lead to an early adoption of and investment in what would quickly become the most important, groundbreaking technology on the planet.

Arnie Bellini began his career at Price Waterhouse just as personal computers began their evolution from space-age technology to household necessity. Realizing the potential of this type of tech, he quit his consulting job, founded a company to help small businesses optimize their servers, and never looked back.

Bellini is co-founder and former CEO of ConnectWise, a provider of IT services to companies in the Tampa market and the publisher of the industry's most widely-used business operating system.He currently serves as managing partner of Bellini Capital, an investment firm based in the Tampa area.

Listen to today’s episode of Investing in Florida Technology and learn Bellini’s start-up origin story at the dawn of the PC, why he believes it’s so important to balance your work life with family and hobbies, and how he equates the lessons he gained training to swim the English Channel to his business philosophy.

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Some Questions Asked:

What was the dynamic like between you and your brother when you started your company as business partners? (03:32)
When you started, did you envision that you would be building a company that you would sell for over a billion dollars? (04:24)
When was the tipping point when you realized that you had become more of a software company? (11:08)
How is your family involved in Bellini Capital? (16:18)
What advice would you have for founders out there? (20:13)
What kind of investments and things are you looking for that excite you? (24:32)

In this episode, you will learn:

A bit about Bellini and his experience as a founder of ConnectWise. (02:09)
How Bellini became a programmer—out of necessity. (08:24)
About Bellini’s experience becoming one of the few people over 50 to swim the English Channel. (12:52)
How Bellini Capital is working to help preserve the Florida Wildlife Corridor. (16:56)
The importance of work/life balance in order to avoid burnout as an entrepreneur. (21:52)
What Bellini finds most exciting in the world of up-and-coming technology. (27:41)

Connect with Arnie:

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

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

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

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

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

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

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

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

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

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

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.

Listen on Spotify

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Some questions asked:

How did the investing in Netflix come about? (02:47)
When did you realize Netflix is really something special? (14:17)
What do you look for in founders? (18:03)

In this episode, you will learn:

Paul’s journey to where he is today. (00:54)
The landscape of venture capital in the late ‘90s. (06:02)
The challenges faced by Netflix in its early beginnings. (08:36)
How Chegg became a decacorn. (20:23)
Linda Yates’ journey to founding Mach49. (24:41)
The five preconditions for success. (27:04)
The reason more and more people are migrating away from Silicon Valley. (30:33)

Connect with Paul:

Resources:

Something Ventured – the movie

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Adam Struck - New Lands of Opportunity Dec 22, 2020

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

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

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

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:

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

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

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

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

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Scott Gorlick - The Future of Investing Feb 04, 2020

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

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

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:

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

Stuart Bertron - Assessing Investment Situations Aug 13, 2019

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

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

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

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)