Connor Tomkies

Why Health Is a Founder’s Secret Weapon with Anthony Ng Monica (Daily Body Coach)

27K views · 9mo ago · 46:59

Guest: Anthony Ng Monica

Anthony Ng Monica started his first business at age 12, exited a global e-commerce SaaS company after more than a decade, and now helps post-exit founders use health as a competitive advantage. In this episode, Anthony breaks down what it really takes to build, pivot, sell, and start again—this time with health, longevity, and energy at the center.

Topics: Exiting SaaS & Using Health as Leverage · Starting Businesses at 12 and Early Sales Lessons · The SaaS Company Anthony Built and Sold · Early Product Failure and Monetization Reality · Selling Before Building and Landing Tesco · Iteration, Pivots, and Long Founder Journeys

Building the Investment Bank for the 99% with Flippa's Blake Hutchinson

20K views · 9mo ago · 45:44

Guest: Flippa's Blake Hutchinson

Topics: Welcome to Made It · Introducing Blake and Flippa · How Flippa works · The investment bank for 99% · Why this market is nascent · Blake’s background and path

How Arjun Mahadevan Is Helping One Billion Entrepreneurs

18K views · 9mo ago · 41:13

Guest: Arjun Mahadevan

In this episode of Made It, Connor Tomkies sits down with Arjun Mahadevan, founder and CEO of Doola, to unpack the journey from idea to company formation—and everything in between. Arjun shares how Doola has helped over 10,000 founders get started, the mindset shift required to go from -1 to 0, and why the first sale matters more than forming an LLC.

Topics: Starting Line Is Negative One · Confidence Through Incorporation · First Sale Over Perfection · How Doola Got Its First Customer · Talk First, Build Later · Rise in Business Formation

From Startup Grind to Generational Wealth: Advice for Founders with Michael Schulte

215 views · 1y ago · 33:35

Guest: Michael Schulte

In this episode of Made It, Connor Tomkies sits down with Michael Schulte, a partner at WestPac Wealth Partners who has spent over a decade helping entrepreneurs navigate the gray space between their business and personal finances. Michael shares the often-overlooked strategies founders need before and after a major liquidity event, like selling your company and waking up with $20 million in your bank account.

American-Made Watchmaker takes on Billion-Dollar Goliath | RT Custer & Vortic Watches

7.8K views · 1y ago · 42:37

RT Custer turned a passion for nostalgia into two thriving American watch brands: Vortic Watch Co., which transforms antique pocket watches into wristwatches, and the ambitious Colorado Watch Co., aiming to bring American watchmaking back at scale.

Topics: Starting in the Memory Business · Why Vortic Turns Pocket Watches · Kickstarter Launch and Early Proof · The Watch-a-Day Marketing Model · Pivoting During the Pandemic · The Story in Every Watch

How “Boring” Businesses Make Big Money with Nick Huber (& Alex Lieberman)

33K views · 1y ago · 49:24

Guest: Nick Huber

Entrepreneur and investor Nick Huber joins Connor Tomkies and Alex Lieberman to break down how he built a $100M+ empire starting with sweaty, unsexy businesses like student storage. They discuss his new book The Sweaty Startup, the trap of chasing big ideas too early, and why momentum, urgency, and simplicity often beat innovation.

Topics: The Problem with Big Ideas · Bootstrapped vs. Venture-Backed · Why Sales is Everything · Deadlines, Profit, and Killing Ideas · Urgency and Entrepreneurial Speed · Momentum and the Grind

📖 Mentioned book: Sweaty Startup Doing Boring Things

Scaling Startups to Zebras, Unicorns & Decacorns with Barry Stamos

45K views · 1y ago · 41:37

Guest: Barry Stamos

We sit down with Barry Stamos, a post-exit founder and investor focused on bold, world-changing companies. Barry shares his journey from corporate consultant to tech founder (Unicorn/IPO/Exit to Oracle), detailing his early struggles, successful exits, and how he now supports other entrepreneurs through Supernova, a collective of exited founders backing groundbreaking startups.

Topics: Kickoff · Welcome Barry Stamos · Leaving Corporate to Build Startups · The Matrix and a Life Pivot · Early Startup Struggles · Building a Billion-Dollar Exit

He Built 52 Hotels and Advised AirBnb with Chip Conley

165 views · 1y ago · 50:24

Guest: Chip Conley

In this episode Connor sits down with hospitality legend and Modern Elder Academy founder, Chip Conley. From building Joie de Vivre into one of the largest boutique hotel brands in the U.S., to mentoring the Airbnb founders through their explosive growth, Chip shares the behind-the-scenes stories that shaped his career and personal transformation. He opens up about near-death experiences, midlife awakenings, and the powerful wisdom that comes from reinvention.

Topics: Who is Chip Conley? · Building Boutique Hotel Empire · Near-Death Experience Changes Everything · Struggles After Selling the Business · Joining Airbnb as Modern Elder · Wisdom Beats Knowledge Today

Surprising Stories About Building a Hotel Empire with Chip Conley

15K views · 1y ago · 51:18

Guest: Chip Conley

In this episode Connor sits down with hospitality legend and Modern Elder Academy founder, Chip Conley. From building Joie de Vivre into one of the largest boutique hotel brands in the U.S., to mentoring the Airbnb founders through their explosive growth, Chip shares the behind-the-scenes stories that shaped his career and personal transformation. He opens up about near-death experiences, midlife awakenings, and the powerful wisdom that comes from reinvention.

Topics: Introducing Chip Conley · Early Career and Real Estate · Building Joie de Vivre Hotels · Near Death and Wake-Up Call · Letting Go of Ego Identity · Midlife Reflection and Reset

From Dot-Com to Giant Exits with Author and Entrepreneur Lewis Schiff

111 views · 1y ago · 38:35

In this episode guest Lewis Schiff—a seasoned entrepreneur, author, and former dot-com founder—shares his journey from early entrepreneurial days to successful exits and strategic angel investing. Lewis dives into his experiences in the dot-com era, explains how technology is transforming traditional industries, and reveals insights on building wealth through founder-friendly capital and innovative business models.

Topics: Entrepreneurial Origin Story · Dot Com Wealth Creation · Early Exit and Real Estate · Angel Investing & Scale Strategy · Tech Drives Business Change · Writing for Wealth Creation

From Dot-Com to Giant Exits with Author and Entrepreneur Lewis Schiff

15K views · 1y ago · 39:28

In this episode guest Lewis Schiff—a seasoned entrepreneur, author, and former dot-com founder—shares his journey from early entrepreneurial days to successful exits and strategic angel investing. Lewis dives into his experiences in the dot-com era, explains how technology is transforming traditional industries, and reveals insights on building wealth through founder-friendly capital and innovative business models.

Topics: Entrepreneurial Origin Story · Dot Com Wealth Creation · Early Exit and Real Estate · Angel Investing & Scale Strategy · Tech Drives Business Change · Writing for Wealth Creation

Failing Fast, Winning Big, and Giant Fire Blankets with Mike Lloyd

74 views · 1y ago · 48:11

Guest: Mike Lloyd

We sit down with Mike Lloyd, a seasoned entrepreneur who built and exited Corvus, a cyber insurance company, for nine figures. Mike shares his journey from Virginia Military Institute to MIT and Harvard, diving into the lessons learned from his first failed startup and how he pivoted to massive success. He also discusses his latest ventures, including a high-net-worth insurance agency and an innovative wildfire protection company.

Topics: Welcome to Made It with Connor · Mike Lloyd’s entrepreneurial journey begins · From MIT to startups and HBS · What business school really teaches · Learning entrepreneurship on the job · The art of networking and relationships

Failing Fast, Winning Big, and Fire Blankets with Mike Lloyd

27K views · 1y ago · 49:05

Guest: Mike Lloyd

We sit down with Mike Lloyd, a seasoned entrepreneur who built and exited Corvus, a cyber insurance company, for nine figures. Mike shares his journey from Virginia Military Institute to MIT and Harvard, diving into the lessons learned from his first failed startup and how he pivoted to massive success. He also discusses his latest ventures, including a high-net-worth insurance agency and an innovative wildfire protection company.

Topics: Welcome to Made It with Connor · Mike Lloyd’s entrepreneurial journey begins · From MIT to startups and HBS · What business school really teaches · Learning entrepreneurship on the job · The art of networking and relationships

From College Dorm to Wall Street IPO with Purpose Built's Miles Lasater

59 views · 1y ago · 31:49

Guest: Purpose Built's Miles Lasater

Episode Description Connor sits down with Miles Lasater, founder of Purpose Built and co-founder of multiple successful companies, including HireOne, which went public in 2010. Miles shares insights on scaling a business from college startup to IPO, hiring a CEO as a young founder, and the challenges of breaking into difficult markets like higher education and government. He also discusses his venture studio, Purpose Built, and the innovative startups he's helping to launch.

Topics: Welcome Miles Lasater · Founding Higher One in College · The Advantage of Naivete · Painting Through Uncertainty · Scaling to 1,000 Campuses · Hiring a CEO as Founders

From College Dorm to Wall Street IPO with Purpose Built's Miles Lasater

21K views · 1y ago · 32:42

Guest: Purpose Built's Miles Lasater

Connor sits down with Miles Lasater, founder of Purpose Built and co-founder of multiple successful companies, including Higher One, which went public in 2010. Miles shares insights on scaling a business from college startup to IPO, hiring a CEO as a young founder, and the challenges of breaking into difficult markets like higher education and government. He also discusses his venture studio, Purpose Built, and the innovative startups he's helping to launch.

Topics: Welcome Miles Lasater · Founding Higher One in College · The Advantage of Naivete · Painting Through Uncertainty · Scaling to 1,000 Campuses · Hiring a CEO as Founders