How To Succeed On the Road to Entrepreneurship

Podcast Summary

This episode of the How To Succeed Podcast features watch entrepreneur Alan Tsao of the Tsao Baltimore Watch Company, tracing his journey from childhood fascination to launching a successful watch brand. After an initial manufacturing failure and losing early partners, Alan persisted, refined designs, leveraged mentorship, and achieved a breakout 2017 Kickstarter that far surpassed its goal via low-cost, gamified marketing.

Tsao built trust with global manufacturers through in-person visits, grew through proactive behaviors and strategic partnerships (National Bohemian, McCormick Old Bay Seasoning, the Baltimore Ravens, the Baltimore Orioles, and the University of Maryland Athletic Dept.), and is developing notable projects like a Francis Scott Key Memorial Bridge watch - using actual bridge steel - with profits donated to victims’ families after the fatal bridge disaster in March, 2024.

Join us, as Alan emphasizes attitude, learning from failure, community-building, and advises aspiring entrepreneurs to take action and, “Just Do It".

 

Chapter 1: Introduction to the How to Succeed Podcast

00:00:02 – 00:00:40 Dave Mattson frames the show’s focus on the “success triangle” of attitudes, behaviors, and techniques. He sets expectations for peeling back how top performers think and act.

Chapter 2: Meet the Guest and Topic

00:00:40 – 00:01:15 Host Chris McDonald welcomes guest Alan Tsao of Tsao Baltimore Watch Company and outlines the plan to explore Alan’s entrepreneurial journey. Alan acknowledges the journey’s challenges and rewards.

Chapter 3: From Childhood Fascination to Passion Project

00:01:15 – 00:03:35 Alan traces his love of watches to a gift at age ten and explains his obsession with mechanical movements. As his career advanced, he built a 35–40 watch collection before deciding, with a nudge from his wife, to start designing his own watches.

Chapter 4: Early Missteps and Losing Initial Partners

00:03:35 – 00:07:03 While working in property management, Alan looped in executives as early partners and sourced a manufacturer via a quick Google search. The first prototypes were low quality, scaring off his partners; he refunded them and bootstrapped forward, seeking advice from other microbrands to refine designs and supply chain.

Chapter 5: Attitude—Learning From Failure and Pushing Forward

00:07:03 – 00:11:23 Prompted by Sandler’s “attitude” lens, Alan reframes failure as learning rather than stopping. He emphasizes determination, confidence, and never giving up, aligning with the concept of “failing forward” to refine processes.

Chapter 6: Breakthrough Kickstarter and Lean Marketing

00:11:23 – 00:14:58 After vastly improved prototypes, Alan launched a 2017 Kickstarter with a $45,000 goal, surpassing it in three hours and finishing at ~$115,000. He attributes traction to a $500–$800 gamified referral campaign that generated ~2,000 emails and ~25% conversion.

Chapter 7: Global Sourcing and Trust-Building

00:15:13 – 00:17:57 Between 2017 and 2022, Alan traveled to Hong Kong and Switzerland to meet manufacturers. In-person relationships built trust, improved terms, and elevated product quality, strengthening credibility and operational know-how.

Chapter 8: Going Full-Time, Investor Catalyst, and Hypergrowth

00:18:38 – 00:23:03 Weighing life choices post-Covid, Alan met an investor through a retail event who first commissioned 250 custom watches, then offered capital. After due diligence and valuation work, Alan accepted the deal, resigned, and the company grew 150–200% the following year.

Chapter 9: Behavior—Showing Up Leads to Opportunity

00:23:03 – 00:23:53 Chris highlights the behavioral discipline of attending events and hustling while employed. Proactive behaviors, not chance, drove encounter-based breakthroughs and subsequent growth.

Chapter 10: Strategic Partnerships—Natty Boh, Old Bay, Orioles, Ravens

00:23:53 – 00:27:47 Alan details collaborations beginning with National Bohemian via Instagram outreach and a fortuitous family contact leading to McCormick/Old Bay. Successive momentum earned projects with the Ravens and an official licensing partnership with the Orioles to cement local brand identity.

Chapter 11: The Key Bridge Watch—Local Manufacturing and Giving Back

00:27:47 – 00:30:33 Tsao Baltimore is producing a watch using actual steel from the collapsed Francis Scott Key Bridge, with 85% of components made in Maryland. All profits support victims’ families, while the project advances local manufacturing R&D.

Chapter 12: Expanding into Education and Sports Memorabilia

00:30:21 – 00:34:27 As official timepiece of University of Maryland Athletics, Alan plans “class watch” programs for schools as an alternative to rings. He previews an Orioles initiative using player-worn jerseys as mystery watch dials with signed player cards, enabling community trading events.

Chapter 13: Proudest Moments—First Sale and Family Validation

00:34:27 – 00:36:48 Alan recalls the emotional impact of the first full-price online sale. A second defining moment came when his young son said, “I’m proud of you, daddy,” affirming the deeper family purpose behind the business.

Chapter 14: Capabilities and Services at the New Workshop

00:36:48 – 00:37:24 The new facility houses certified watchmakers capable of servicing luxury brands, acting as a U.S. repair hub for jewelers and independent watch companies.

Chapter 15: Advice to Aspiring Entrepreneurs

00:37:24 – end Drawing on his teaching at the University of Baltimore, Alan urges aspiring founders to start, learn by doing, and iterate through trial and error. He stresses overcoming comfort zones, accepting risk, and avoiding regret by taking the first step.