Dot‑com Crash, Losing Millions, and Opening a Bar

In this episode of the ASOM Pod, hosts Jimmy Kim (CEO of eCom Email Marketer & Commerce Roundtable, formally Founder of Sendlane), John Roman (CEO of BattlBox), Amer Grozdanic (CEO of Praella), and Bryan MacDonald (Direct of eCommerce at Oma’s Pride) sit down with Curtis Masco, Founder and CEO of Portland Leather Goods, for one of the most raw and inspiring founder stories you’ll hear.

From living in a Zen monastery to building one of North America’s largest leather manufacturing operations, Curtis shares how continuous reinvention became his blueprint for success.He opens up about overcoming alcoholism, self-funding every stage of growth, and why he believes you have to “kill 90% of what got you to your first million” to reach the next level.

What you’ll learn in this episode:

- How to reinvent your business every year to stay ahead.

- The philosophy behind building and rebuilding momentum.

- Lessons from scaling from art festivals to Etsy to Shopify.

- Why self-funding beats chasing investors (and how he did it)

.- How Curtis overcame personal struggles to unlock his potential.

- The importance of surrounding yourself with the right people.

- Why belief, integrity, and confidence matter more than capital.

- The future of craftsmanship, eCommerce, and personal growth.

Whether you’re in the grind of your first startup or looking for the spark to level up again, this episode is proof that reinvention isn’t just possible.. it’s powerful.

Follow Curtis on YouTube → youtube.com/@CurtisMatsko for more unfiltered business lessons, founder stories, and behind-the-scenes of Portland Leather Goods

Big shoutout to our sponsors who make this podcast possible

Omnisend — With 125,000+ eCommerce merchants, Omnisend is the all-in-one email & SMS marketing platform built to deliver seamless, personalized experiences via email and sms with ease. Learn more at https://www.omnisend.com/

Kintsugi — AI that monitors, files, and optimizes sales tax for you. Eliminate your tax headaches forever. Mention ASOM for 3 months free at https://www.TryKintsugi.com

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00:00 Teaser Trailer

00:40 Welcome to the ASOM Pod

02:16 Special Guest Introduction: Curtis Masco of Portland Leather Goods

05:02 Curtis Masco's Early Life and Zen Monastery Experience

08:06 The Dot-Com Crash and Starting Over

10:21 Building Portland Leather Goods: Growth and Sobriety

12:12 The Power of Belief and Manifestation

16:48 Investing in Founders and Giving Back

21:26 The Importance of Self-Belief and Surrounding Yourself with the Right People

35:17 The Importance of Integrity, Motivation, and Intelligence

36:47 Lessons from Business Failures and Successes

37:56 Reinventing Your Business Every Year

39:36 From Art Festivals to eCommerce Success

42:11 Navigating Manufacturing Challenges During COVID

43:25 The Future of Business and Personal Growth

01:02:07 The Power of Networking and Social Media0

1:06:11 Closing Remarks and Final Thoughts

Contact us at hello@asompod.com for sponsorships, appearance requests, interviews, or general information!

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