Omslagafbeelding van de show “Bend”ing Rules

“Bend”ing Rules

Podcast door Pete Ozolin; peter@achieve-one.com

Engels

Business

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Over “Bend”ing Rules

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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31 afleveringen

aflevering Bending Rules -- Dood Woof CEO, Elina Panteleyeva explains how she went from being fired to starting a company that generated 650K in its first year and is on target to more than double sales in 2025 artwork

Bending Rules -- Dood Woof CEO, Elina Panteleyeva explains how she went from being fired to starting a company that generated 650K in its first year and is on target to more than double sales in 2025

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 disadvantage on some fronts. However, entrepreneurs like Elina make the murky waters a bit clearer. After being let go from her job at an AI company, Elina decided to take the proverbial entrepreneurial leap. With not much experience in e-commerce or retail, she followed her passion and founded Dood Woof, a company that offers organic shampoo and detangler for doodle dogs. Niche, right? In her first year, she realized revenues of $650,000 and is projecting $1.5 million in her second year of operations, with more products to follow. Elina financed her own efforts, and what she lacked in experience she more than made up for with tenacity and her authentic, thoughtful approach to building her brand to this point. If I were contemplating any sort of e-commerce start-up, I'd tune into this episode.Onward ~ 3:42 -- Elina's background and the birth of Dood Woof 16:54 -- Building a community and landing a product 28:14 -- Leveraging micro influencers for brand growth 30:25 -- Sales strategy: Amazon vs Direct Website Traffic 38:28 -- Financing growth 42:27 -- Utilizing AI in Business Operations 44:27 -- Establishing culture and values early

27 apr 2025 - 44 min
aflevering Bending Rules -Chris and Jeremy, founders of 10 Barrel Brewing Co, which they built and guided to a successful exit to Anheuser-Busch in 2014, share the ups and downs of that journey and what followed artwork

Bending Rules -Chris and Jeremy, founders of 10 Barrel Brewing Co, which they built and guided to a successful exit to Anheuser-Busch in 2014, share the ups and downs of that journey and what followed

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. With a lucrative exit to Anheuser-Busch in 2014, which could have allowed them to sail off into the sunset, the Cox brothers continued to invest in and give back to the communitythat supported their efforts for over a decade. They created a restaurant group, invested in other beverage businesses, and support a handful of angel investments that they continue to nurture today. As I visited with the brothers, I learned that their story is much more than what has been one of Bend’s most visible business sales. The seeds of their entrepreneurial spirit were formed much earlier in life, and 10 Barrel represented a culmination of their passion for doing work they enjoyed, leaving lucrative corporate jobs—like so many entrepreneurs have to decide to do in order to follow their dreams. The company they built was by no means an overnight success; like many successful businesses, it was achieved throughyears of hard work, sacrifice, and tough lessons. Even after the sale in 2014, it wasn’t until 2024 that the brothers resigned from the parent company, working in tandem, of course, as they continued to refine their knowledge witha much larger operator. Every entrepreneur's outcome offers a unique opportunity to learn and be inspired. While aspects of the Cox brothers' efforts are similar to those of other company builders (hard work, timing, etc.), there were some key inflection points I found interesting, such as their ability to quickly integrate lessons learned from their mistakes and clearly understand each other’s strengths as they ventured into an industry in which they initially had little experience. As Chris Cox stated in 2014, recalling their first investment in a local bar in 2003, “The bar was super reasonable. We had never worked in bars before or anything. We just wanted to get to Bend; we couldn’t find any other way to get there for jobs, so we bought a bar.” A few years later, in 2007, the idea for 10 Barrel Brewing was born. I’d argue that passion for an industry is often the first step to taking the proverbial leap of faith to embark on one’s own path. However, it was clear to me after our conversation that these brothers are shrewd businesspeople. While they enjoy the task of building a brand and the team they work with, they understand market dynamics. Drawing on tough lessons from their past, they were able to position 10 Barrel for a successful exit while continuing to do the community work they love. 2:51 -- Early influences and family background 7:47 -- First venture and learning experience 10:51 -- Transitioning from corporate world to entrepreneurship, start-up capital (boot-strap) 14:42 -- The birth of 10 Barrel Brewing 23:02 -- The breakthrough! Hiring key talent 32:23 -- Importance of mentors and learning to accept rejection from prospective investors 37:05 -- A "chip" on the shoulder helps. "Losers think about winners, and winners think about winning" 40:07 -- Recession seeded a strategy to grow outside the region: the "taking of their first handle" 50:08 -- The decision to sell the company, past mistakes inform them "timing matters" 56:14 -- After the acquisition, the amazing partnership with Anheuser-Busch (note, it doesn't always go this way:)). 1:00:59 -- Transitioning to new ventures -- what now? Current projections and future directions.

9 apr 2025 - 1 h 7 min
aflevering Christa King, a two-time startup founder, and I dive deep into failure and explore where to find the fortitude and drive to start again artwork

Christa King, a two-time startup founder, and I dive deep into failure and explore where to find the fortitude and drive to start again

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 platform for the hospitality industry, which she ultimately decided to shut down. As folks are aware, we spend a lot of time on the Bending Rules Podcast sharing stories of entrepreneurs who have built companies and found meaningful exits. While we do on the pod discuss failures and challenges, Christa and I decided in advance to dive deeply into the topic of failure—why it happens, what we can learn from it, and perhaps why it isn’t discussed more. Likewise, we explored what it takes to recover from a failed venture. Not surprisingly, Christa sees a failed venture as a learning opportunity and a part of the process. We can learn a lot from her attitude toward failure and setbacks. Now, as the founder of Cricket Fixes, she’s building the #1 marketplace for self-development courses and transformational retreats.  As always, I hope we all learn something we can take forward. Onward, Pete 1:00 -- Intro to Entrepreneurship and Failure 4:02 -- Christa discovers entrepreneurism 8:28 -- Founding of Fitlandia 13:29 -- Did sticking to her values cost Christa her company? 21:40 -- Learning from failure 32:20 -- Next venture, building Cricket Fences 41:33 -- Generational slides in mental health and awareness 49:36 -- Role of financial success and purpose

7 mrt 2025 - 53 min
aflevering Bending Rules | Michael Ulin, Co-Founder of Paxton AI, a legal technology company that recently closed a $22 million Series A, shares his journey into entrepreneurship and how it led him to Paxton AI artwork

Bending Rules | Michael Ulin, Co-Founder of Paxton AI, a legal technology company that recently closed a $22 million Series A, shares his journey into entrepreneurship and how it led him to Paxton AI

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, Michael embarked on a journey that would take him far beyond the confines of his small-town upbringing. His career began at McKinsey & Company, where he met his future co-founder, Tanguy Chau. This pivotal connection would later lead to the creation of his company, Paxton AI. Michael’s venture into the world of AI began with his roleat RPX, a legal tech company that sparked his interest in AI and set the stage for his future endeavors. After RPX, Michael co-founded Zesty AI with several former McKinsey colleagues. At Zesty, he served as the head of AI, applyingadvanced AI models to the property insurance industry. “That was my first startup from inception to the growth stage, and I learned a lot along the way and made a lot of mistakes. It set me up well for what we’re doing today at Paxton AI.”  Michael’s journey has not been without its personalstruggles. Like many McKinsey alumni, he considers himself an “insecure overachiever,” a mindset that drove him to excel but also left him vulnerable during tough times. “At Zesty, my identity was tied up in the company’s success, and when we struggled financially, I felt like I had failed.”  However, as with most successful entrepreneurs, Michael recognized that failure is just another learning opportunity. When the opportunity to partner with Tanguy Chau andco-found Paxton AI arose, he seized it with enthusiasm. “The early stages of company building were the most exciting to me at Zesty. When generative AI came to the fore, and Tanguy and I saw the potential, we jumped at the chance tobuild something new,” he says. Together, they created Paxton AI and the industry is taking notice! Onward, Pete 2:47 -- Introduction to entrepreneurship. 6:58 -- Co-founding Paxton AI and its mission 12:15 -- Getting technical, navigating the speed of innovation within AI frameworks 23:37 -- LLM vs SLMs, what's the difference? Why domain expertise is the winning ingredient 30:54 -- The linear success path straight up to the right is rarely the case, how failures shaped his path to success 35:21 -- What's is take to get VC funding (now having been apart of several founding teams that have raised VC) 50:53 -- Cultivating culture with a remote workforce and parting thoughts

27 feb 2025 - 56 min
aflevering 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 artwork

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

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, the ultimate answer to that question was “no.” It took me two years to figure that out, and I have zero regrets about having brought on a CEO, which ultimately put the company on a different trajectory, culminating in a successful exit. To this end, it was fun to have Mark Josephson join the podcast this past week. Mark was brought in as a "CEO for hire" twice: first at Bitly, where he successfully grew the team and achieved an exit to Spectrum in 2017, and before that, he helped Seevast reach over $100M in revenue in 2006. He subsequently built and sold Outside.in to AOL in 2011. Even with those successful outcomes, Mark had to scratch his “founder” itch and started Castiron as founding CEO, a company that was acquired in 2024. Mark shares the difference between being hired as a CEO and being empowered to lead versus the connection that team members have with founding CEOs, where the leadership inspiration often comes from within that founder, creating an implicit trust. Regardless of one’s approach, Mark demonstrates that it can work in either capacity. I encourage founders to look inward and then create a team formula they believe will give them the best probability for success, egos aside. Our discussion can be found below. 1: 00 -- Bending Rules kicking off year 2 3:59 -- Hired twice as CEO for start-up/early stage companies 8:09 -- How to find those early mentors 15:56 -- Transition from employee to entrepreneur 23:43 -- Difference in CEO roles if founder versus hired gun 30:48 -- Empowered to lead versus power w/in to lead 43:22 -- Challenges along the way and near death experiences (for the companies that is) 49:01 -- Traits of a successful entrepreneur 54:54 -- Can you find balance as an entrepreneur?

27 jan 2025 - 59 min
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