“Bend”ing Rules

Jan 27 2025 27 ep. 66 mins 36

“Bend”ing Rules Podcast artwork

It is difficult to choose the entrepreneurial and risk-taking path. I made that decision, and after a lot of mistakes, I eventually found a balanced life that resulted in more time with family, friends, and the community. This podcast will focus on the lessons and experiences of successful (and sometimes not-so-successful) entrepreneurs and rule-breakers who have endured along their journeys and found positive outcomes—whose efforts were the result of deliberate approaches, not those of starry-eyed 'unicorns,' but rather committed, determined company builders and visionaries.

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Bending Rules - Mark Josephson, former CEO of Bitly and later founder of Castiron, discusses the trade-offs in hiring an outside CEO versus navigating the journey as a founding CEO

Jan 27 2025 59 mins

Intro: One challenge in growing a company, especially as a first-time entrepreneur, is answering the question, “Am I the right person for the CEO job at this time?” I’d say that in the VC world, there’s a bias toward having a founder continue in the capacity of CEO. But what if that founder isn’t gaining investment traction or lacks industry expertise? In my first start-u

Rob Little, CEO of Cairn, a company he co-founded in 2014 and acquired by Outside Magazine in 2021..

Dec 19 2024 62 mins

Intro: Rob Little, former CEO and Co-Founder of Cairn—a discovery platform founded in 2014 and acquired by Outside Magazine in 2021—joins Bending Rules to share his journey into entrepreneurship and the eventual founding of Cairn. As one might expect, the path wasn’t linear. Once an aeronautical engineer with Lockheed Martin and a newly minted graduate of the University of Pe

Bending Rules - Dan Hobin, Founder/Former CEO of G5, one of Oregon's most successful SaaS companies in the last couple of decades, employing ~250 people when acquired in 2021

Dec 05 2024 71 mins

Intro: Dan Hobin’s name is synonymous with entrepreneurship in the state of Oregon. He first gained recognition as the co-founder and CEO of G5, a SaaS company he led to become one of Oregon’s most successful software companies over the last decade. During his tenure, G5 was recognized by Inc. magazine as one of the fastest-growing private U.S. companies and by Deloitte as one

Bending Rules -- Alan Rich, most recently Founder and CEO of Chrome River, a company that was acquired for 520M in 2019, shares his journey and what keeps him inspired to keep creating companies.

Nov 20 2024 60 mins

Intro: Alan Rich, a lifelong entrepreneur, is likely best known as the former Founder and CEO of Elite Information Systems, a company that was acquired by Thomson Reuters, as well as later being a Founder and CEO of Chrome River, which was acquired by Emburse in a transaction valued at approximately $520 million. He has now found a way to come full circle in his experience as a com

Scott Allan, CEO of Hydro Flask, a consumer product company that he guided from $2 million in sales to $100 million in a four-year period (2012-2016), is a story worth telling.

Nov 07 2024 91 mins

Intro: Scott Allan, Former CEO of Hydro Flask, a consumer product company that he guided from $2 million in sales to $100 million in a four-year period (2012-2016), is a story worth telling. Many aspects of Scott’s and his team’s journey are obviously impressive, but what I enjoyed most was his candor about the challenges, if not failures, he faced along the way. His background

Bending Rules -- Monica Enand, CEO & Founder of Zapproved, shares her incredible and inspiring journey, including growing a company to 170 employees, and navigating the company to an exit in 2023

Oct 29 2024 68 mins

Intro: It’s not every day you have a chance to interview someone who was a successful start-up founder and, initially in her words, “a stay-at-home mom” who was bored. She went on to discover a product category where her domain expertise was limited, led a minority equity round with a private equity firm(K1), took on a majority equity partner (Vista Equity Partners), and late

"Bend"ing Rules - Taylor Welsh joins as employee #1, several years later assumes the CEO position and leads company to a successful exit in 2022. She's now onto her next exciting start-up.

Oct 22 2024 66 mins

Intro: Taylor Welsh joined Walker Tracker as employee #1, several years later she was elevated into the CEO role by the founder. From there, Taylor successfully grew the business and navigated the company to a successful exit in 2022. Taylor has quality that I like to see in entrepreneurs and as a former guest, Bayard Fox, referred to as a “quite confidence” about her. Taylor s

Bending Rules - joined by "solopreneur" Reynolds Maxwell, a successful commercial real estate investor, shares journey from Corp America into solo entrepreneurship vs joining a smaller co or start-up

Oct 14 2024 75 mins

Intro: Entrepreneurship is not a "one size fits all" type of endeavor. I have always been fascinated why some people want to build companies and others are more comfortable operating alone. What characteristics make you more inclined one way or another? From Reynolds we learn that teamwork and a reliable network of partners is still vital whether you are a company builder or solopr

"Bend"ing Rules -- from a team that raised 36M in a funding round, to boot-strapping his next venture, Nick McEvily doesn't sit still

Oct 10 2024 64 mins

Intro: Nick was fortunate to cross paths early in his career and become a co-founder of a team where Mark Cuban participated in a large financing round. Having said that, Nick's experience taught him that raising the money isn't the goal, it's building a sustainable business. Further, my interview with Nick confirms that if a founder leans into their strength(s) (be it sales, opera

"Bend"ing Rules - Dan O'Day leaves Thompson Reuters to start ECFX, 5 years later the business is thriving; learn more about raising money, earning a customer's trust and jumping in with both feet

Sep 24 2024 68 mins

Intro: It’s never too late to start a company, but in some ways it’s likely more difficult the longer one waits to take the proverbial jump, especially in the event you reach the “golden handcuff” stage as our guest, Dan O’Day, did when he became a VP at Thomson Reuters (TR), where he spent the better part of twelve years. TR, for those that aren’t as familiar with, is