Technically Speaking
Technically Speaking with Harrison Wheeler
The First Step: Stephen Green's Lessons Learned as an Entrepreneur and Investor

The First Step: Stephen Green's Lessons Learned as an Entrepreneur and Investor

What does it take to start a business? Is it by having the money or by having investors? Does it depend on having social capital? Or both?

Would you believe that it all starts in your head? It all starts with ONE idea that solves a problem. And it's not impossible that 3,000 miles away, someone will pay for that solution you came up with.

By taking that first baby step, you're choosing to embark on your journey, from which you'll learn a lot, whether it becomes successful or not.

Listen to this episode with Stephen Green to learn about how he started his career in finance and as an entrepreneur. Learn how he uses his background to support Black-owned businesses in Portland through PitchBlack, and how he helped A Kids Book About to start challenging, empowering, and important conversations with kids.

About the Guest:

Stephen Green (he/him) from Portland, Oregon is a Blatino who has spreadsheets as his super power and sneakers as his kryptonite. As a result of living in Portland his whole life, he's become a person that gobbles up relationships and community. Like most entrepreneurs, his journey began with his parents who were both entrepreneurs while he was growing up. While his mom started a tech company, his dad worked for Intel for a long time before starting his own HR company with Intel as their main client. And he’s now passed this on to his oldest daughter, who also started a business during the pandemic and now takes him out to dinner.

A husband, father, recovering banker, and VC, he’s also the founder of PitchBlack, a pitch competition he started in 2015 that highlights black founders in regions across the country who strive for community over competition. It has expanded to include events in Seattle, Austin, and Philadelphia. And to date, 100 founders have pitched their ideas, more than 1,000 people have attended the combined events, and more than $100,000 has been awarded directly to the winning companies. In addition, the Portland winners have raised an additional $40M in funding since 2015. 

A startup mentor and advisor to portfolio firms at Backstage Capital, he also held positions at these companies: Director of Operations at PENSOLE, COO at A Kids Book About, and Community Director at WeWork. He co-authored A Kids Book About Family and he's a contributor to A Kids Book About Public Speaking by TEDxPortland, a volunteer-driven, nonprofit organization, where speakers and performers share ideas on a wide range of topics to bring people together and spark deep discussion and connection.

Connect with Stephen Green:

  • Twitter: @PDXStephenG

  • Instagram: @PDXStephenG

  • PitchBlack:

  • A Kids Book About:


(02:33) - Icebreaker: How Stephen Green became "The Guy Who Knows Everybody"

(04:06) - Icebreaker: What America looks like through the eyes of immigrants

(04:53) - Icebreaker: His sneaker collection and his three Grail shoes

(07:25) - One of the few things that can give you true gratification

(08:07) - The two kinds of people in the world

(08:44) - His educational background, career in banking, and working with founders

(10:18) - What being part of a community is all about and how you can participate in yours better

(12:16) - PitchBlack's success story

(13:54) - How PitchBlack started and what to watch out for next

(16:53) - Being a Blatino while having his own identity in and out of the home

(19:34) - Why he thinks now is the easiest, cheapest, and quickest time to start a business

(20:45) - The over-glamorized world of entrepreneurship and what you should be focusing on instead before raising money for your business

(23:55) - The core tenets of starting and/or running a business

(25:45) - Ways your Mission, Vision, and Values make or break your business

(27:38) - How Jelani Memory’s A Kids Book About started, how George Floyd’s murder impacted their business, and ways their books bring people together

(31:02) - The two most important pieces of advice he's heard in his 15 years in banking

(32:51) - Why you should never underestimate the power of moving the needle by taking baby steps


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Technically Speaking
Technically Speaking with Harrison Wheeler
Technically Speaking is a podcast by Harrison Wheeler about BIPOC designers, entrepreneurs & technologists sharing their unique stories of triumph and resilience at the intersection of product design.