“Bend”ing Rules

Intro : I have always believed in learning from entrepreneurs younger than myself, which seems to be happening more and more these days, and this episode with Elina Panteleyeva is no exception. It's too easy, as an experienced entrepreneur, to think that you have many of the answers. In today's fast-moving waters with AI start-ups and new methods to reach your audience, I find myself at a...

Intro : I have had the pleasure of interviewing several individuals who have built great companies (Hydro Flask, G5, Cairn, Walker Tracker, etc.) in my hometown (I still see it as a town, despite the significant growth), Bend, OR. Most recently, I sat down with two other well-known businessbuilders, Chris and Jeremy Cox, the brothers best known for starting the brewing company 10 Barrel Brewing Co...

Intro: I was joined by Christa King. Christa has over 30 years of experience in pioneering commercial strategy in hospitality, launching and executing high-impact revenue strategies for some of the world’s most iconic hospitalitybrands—including Ritz-Carlton, Marriott International, Joie de Vivre Hospitality, and Noble House Hotels & Resorts. Christa later ventured into Fitlandia, a wellness p...

Intro: Chris Capdevila and I were joined today by Michael Ulin, most recently a Co-founder of Paxton. AI, a legal technology firm designed to transform the legal landscape with state-of-the-art generative AI tools that expedite and simplify legal research, contract drafting, and review. Paxton AI just closed a 22M Series A financing lead by Unusual Ventures. After graduating from Emory University,...

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-up, when I was twenty-six,...

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 Pennsylvania’s Wharton S...

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 of North America’s f...

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 company builder, wh...

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 as a technology exe...

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 later guided the exit to a...

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 shares in her journ...

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 solopreneur. In either...

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, operations, product,...

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 a company with a global pre...

It is difficult to choose the entrepreneurial and risk-taking path. I made that decision, and, after a lot of mistakes I found a balanced life without having to compromise other needs, such as family, friends and health (most of the time), and, I believe you can do so as well. This podcast will focus on lessons and experiences of successful (and sometimes not so successful) entrepreneurs and risk...

Intro: The path to entrepreneurship comes in all shapes and sizes. That's why when I had a chance to interview Kyle Morris, Special Forces Army Ranger (retd), now a successful entrepreneur (recently realizing an "exit" in 2023 with his start-up), I knew I was in for an engaging dialogue. Translating what he learned from his time in the armed services to the corporate/start-up world w...

Intro: We all have heard war stories on starting companies, but it's even tougher (on some level) if you have take on all the risk yourself. That's what Gabe Ayers did when he bootstrapped Apricity from a company of one (1) to a company of twenty-five (25), before ultimately realizing his exit. Gabe shares how from a young age he connected "ideas" to product/revenue, including at...

Intro: I was happy to have Patrick join to discuss what it means to be an "intrapreneur" at a company as large as Oracle. Patrick is on his second or third stint with Oracle, having left a time or two to start various companies and pursue his other passion of building a real estate portfolio, etc. This episode was a bit emotional for me, Patrick is a long-time friend and in the last coup...

Intro: I am sure more than once many of you have sat behind your comfortable corporate environment and thought "is now the time to take a leap of faith?" Well, Justin Johnson did just that. After a 20 year career in professional services, the last 7 which were at Frank Russell Company and only a year away from a paid sabbatical, Justin decided to launch his start-up, which was successful...

Intro: We have all had a great idea for a restaurant at some point, right? Well, Ian picked his spots to invest and start new brands and restaurant concepts over the past 20 years with some great results, including the co-founding of Lemonade, a California based restaurant chain that expanded internationally, including a restaurant in Dubai. Whether you are aspiring to be a restaurateur or not, Ia...

Intro: While it's great to have so many interviews with entrepreneurs, Eric and I thought it might be good to look back and summarize the last 4-5 guest on the podcast. Where do we see patterns? What's unique to each personality and/or journey? We are calling the "break-out" session and hope to do some of this reflecting/summarizing from time-to-time. 2:00 -- Who should be included in the definiti...

Chris Capdevila joins and shares his upbringing and journey into entrepreneurship and ultimate founding of a company that was acquired by Oracle. I felt like we only scratched the surface with Chris, and look forward to having him join another time. 4:06 -- Role of failure 8:56 -- Role of risk taking, what drove Chris to take a risk and start a company 13:14 -- How upbringing & experience shap...

Entrepreneur John Kelly joins Pete & Eric to share his path to financial independence and perspectives on running a small business, selling it, transitioning careers. In this casual conversation, I walked away with some nuggets of information that the younger me/entrepreneur would have benefited from -- one in particular was understanding the "motive" of everyone involved in a transa...

Intro: Bayard Fox owner of Cement Elegance joins Pete Ozolin & Eric Staley to talk about his entrepreneurial journey and the characteristics he fell back on to build a successful manufacturing company. Great story of perseverance. 3:30 -- Role of "fear" in being an entrepreneur 11:36 -- Business Partners, how an early failure with a business partner shaped his future decisions and su...

2:22 -- Jeff shares lessons in RE and buying first house for $28,000 on seller contract and how from there he built a successful real estate development firm. We couldn't possibly cover everything in an hour to encapsulate Jeff's 30+ real estate development career, but Jeff imparts several insights to help any entrepreneur making the proverbial leap of faith. 7:38 -- Role of mentors and in...