From $50 to $60 Million: Overcoming Business Failure w/ Jay Myers (Founder of Bold Commerce)

The Biz Devo with Kenneth Ott

When Jay Myers' online business collapsed, leaving him unable to pay rent and down to his last $50, it seemed like complete failure. Yet this rock-bottom moment became the foundation for Bold Commerce, which now serves over 800,000 Shopify stores. His journey reveals how business failure often contains the hidden seeds of extraordinary success.

Connect with Jay

• LinkedIn: https://www.linkedin.com/in/jasonnmyers/
• Instagram: https://www.instagram.com/jasonnmyers/
• Bold Commerce: https://boldcommerce.com
• The Shopify 1% Podcast: https://podcasts.apple.com/us/podcast/ecommerce-is-just-math-lets-break-it-down-growth-on/id1785874734?i=1000691385152
• The Shopify 1% Podcast on Instagram: https://www.instagram.com/shopify1percent/

Summary

In this inspiring episode, Ken welcomes his first-ever Grow Time Biz Devo guest, Jay Myers, founder of Bold Commerce. Jay shares his powerful story of overcoming devastating business failure to build one of e-commerce's most successful companies. After his online archery supply business collapsed under mounting debt and logistical challenges, Jay found himself broke, unemployed, and unable to even pay rent. At his lowest point, with just $50 to his name, he had a profound conversation with God about his future that changed his perspective entirely.

This complete business failure became the turning point that led Jay to discover Shopify and identify the app marketplace opportunity that would become Bold Commerce. The company grew to employ 450 people, serve over 800,000 stores, and raise $60 million in funding. Throughout the conversation, Jay explains how his faith helped him navigate the crushing disappointment of business failure and remain open to the unexpected doors that opened when others closed.

The discussion explores crucial principles for entrepreneurs facing failure: understanding the difference between setbacks and defeat, recognizing that valleys are where growth happens, seeing business failure as preparation rather than conclusion, and knowing that our hardest challenges define who we truly are. Jay's journey powerfully demonstrates that overcoming business failure isn't just about persistence—it's about maintaining faith through the valley moments and recognizing the greater purpose being written through our struggles.

Top 3 Growth Tips

• Learn to See Business Failure as Growth: Jay uses the powerful valley metaphor to explain how failure provides essential growth. "What's in the valley? It's lush, it's green. That's where stuff grows. And when you're in the valley, know like, see it for what it is, it might be hard, but you're growing." Your biggest business growth happens in your most challenging seasons. (54:59)
• When One Business Fails, Look for New Doors Opening: Instead of fixating on the business that failed, be attentive to new opportunities emerging. "If a door closes in your life, just be really observant of what other doors are opening. And so many times we cover our eyes and all we can think about is the door that closed." Jay discovered Shopify and the app opportunity only after his previous business completely collapsed. (1:04:19)
• Build a Business, Not Just a Job: After overcoming his business failure, Jay understood the crucial difference between "owning a job" where income stops when you stop working, versus building a true business that can function without you. "With my eBay sales, the day I stopped listing things, I stopped making money. So I owned a really good job, but it wasn't a business." (21:16)

For more tips, discussion, and behind the scenes:

• Follow us on Instagram @iamKenOtt
• Watch us on https://www.youtube.com/@KenOtt

About Ken Ott:

Kenneth Ott is an owner of multiple businesses, entrepreneur, husband, father, and Christian leader. Ken is the co-Founder of Metacake, an Ecommerce Growth Team and Dough Capital. Ken is an author, speaker, and business coach. To connect or learn more, visit:

• KenOtt.com
• Ken on LinkedIn
• Ken on Twitter/X
• Ken on Instagram
• Ken on Facebook
• Metacake - An Ecommerce Growth Team
• Dough - We own amazing DTC brands
  
  

Show Highlights

[0:06] Ken introduces the first-ever guest on the Grow Time Biz Devo podcast, his friend Jay Myers.

[1:25] Ken shares that Jay founded Bold Commerce, one of the first and biggest Shopify app developers.

[2:10] Jay expresses humble gratitude for being invited as the first guest on the show.

[4:31] Jay explains that Bold has grown to around 450 employees and has had over 800,000 Shopify stores use their apps.

[5:05] Jay defines success not by revenue but by lives impacted: "I know that we've had four people who have met at Bold that have got married."

[7:05] Ken acknowledges Bold's tremendous marketplace success in the Shopify ecosystem.

[8:40] Jay discusses the responsibility of having employees relocate their lives to work for his company.

[11:25] Jay shares a profound insight about leadership: "Over-trying to help someone sometimes is actually hurting them."

[15:10] Jay discusses how faith helps release the pressure of leadership: "Every step of their journey, God's not done with you yet."

[16:50] Jay shares his background in competitive archery and starting a family archery business at age 13.

[21:16] Jay explains the key difference between owning a job versus owning a business: "With eBay, I had a job. The day I stopped listing, I stopped making money."

[24:51] Jay describes reaching a breaking point in his online archery business where he maxed out all credit lines.

[30:05] Jay recounts his lowest point: having no money, asking family to help pay rent, and keeping his last $50 bill as a security blanket.

[31:00] Jay shares a profound spiritual moment where God asked him: "How could you ever manage 100 people when you can't even manage yourself?"

[33:00] Ken asks what kept Jay going despite such devastating business failure and discouragement.

[34:32] Jay explains how his sports background taught him that losing a game doesn't make you a loser.

[37:53] Jay tells the story of going through his trophies with his son and then throwing them away: "The value has nothing to do with the trophy."

[41:46] Jay shares the profound metaphor of cross-stitch: what looks like random threads on one side is a beautiful picture on the other.

[46:30] Ken relates to Jay's story with his own current challenges, including a recent injury that has limited his physical capabilities.

[54:59] Jay shares the powerful valley metaphor: "Valleys don't last forever, but that's where your growth happens."