Intro: After being let go from her job at an AI company, Elinadecided to take the proverbial entrepreneurial leap. With not much experience in e-commerce or retail, she followed her passion in working with Doodle Dogs, and started DoodWoof, a company that offers organic shampoo for doodle dogs, niche right? In her first year she realized revenues of$650,000 and is projecting 1.5M 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 in tenacity and in her authentic, thoughtful approach in 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

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.

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

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

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?

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 School (MBA), Rob had numerous options. However, he chose to venture across the country to the northwest and pursue the entrepreneurial path, co-founding Cairn, a company that eventually connected thousands of outdoor enthusiasts to the latest and greatest brands and products in the outdoor industry. Cairn’s subscription platform seeded approximately 34 million products for more than 300 partners and introduced new brands and products to over 75,000 highly qualified enthusiasts throughout the life of the business. As one might expect, I was curious how Rob’s background as an aeronautical engineer benefited him in running a consumer product company. His journey is layered with great tactical advice for entrepreneurs, including reflections on cultural dynamics during growth and contraction, which I found particularly interesting. I left our conversation with the feeling that Rob has another start-up in him. Understanding, of course, the “all-in” aspect of that decision, he’s taking his time with family and friends—perhaps the greatest reward of the journey.

This will be our last episode for 2024, marking the culmination of the first year for the Bending Rules Podcast. I hope folks enjoyed and benefited from these stories. We look forward to continuing to share the stories of entrepreneurs in 2025, and with several great guests already on the calendar, it should be another year of insights and growth.

2:19 -- Rob's background and life prior to entrepreneurship

8:54 -- Shifting from aeronautical engineering to the tought of running an outdoor products company

15:05 -- Wharton School of Business: Opportunity Cost vs. Entrepreneurial Conviction

21:56 -- Data Driven Decision and how engineering background helped inform decision to scale and grow the company

34:07 -- Roller Coaster ride of entrepreneurism

37:39 -- Wild West of Facebook Advertising

44:20 -- Acquisition: challenges and opportunities

53:04 -- Reflections and possible future directions

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 fastest-growing technology companies. From bootstrapping for five years to securing a minority equity round, later a majority equity round, and ultimately an acquisition by RealPage in 2021, Dan and his team accomplished all of this in Bend, Oregon, before the term “Zoom Town” became popular. At the time of the acquisition, the company had an approximate annual recurring revenue (ARR) of $50 million and over 200 employees.

Dan has always given back to the entrepreneurial community, not only as an angel investor but also by sharing his experiences and helping other entrepreneurs in his community. In 2003, he co-founded the Bend Venture Conference (BVC), which is the largest and longest-standing angel investment conference in Central Oregon and the broader Pacific Northwest. The BVC has helped transform a small timber community into a startup mecca and has rewarded over $14 million in angel/investor financing through its BVC Funds, LLC.

We are excited to have Dan share his story on the Bending Rules podcast, as well as how he’s spending his time these days, which, not surprisingly, includes helping startups scale, among other interests. Enjoy.

4:24 - Intro / Early Ventures

6:18 - Lessons from early failures

9:05 - Importance of capital efficiency

11:53 - The drive to start again, building G5, initial steps

26:56 - Bootstrapping vs overcapitalization

33:02 - Expanding into new verticals, growth pains

44:15 - Lessons when 5 years in, what Dan would have done differently

51:13 - Reflection of leadership

56:50 -- Investing in start-ups: insights and criteria

1:07 -- Building and preserving company culture

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, which started with him working side by side with his father. Today, he’s the CEO of Y Meadows, a company that not only delivers an AI-driven solution to customer support teams but that he enjoys running alongside his own sons.

Sitting down with Alan, I not only learned about his unique story in the founding and sale of Elite Information Systems—twice, to two different publicly held companies, the last of which was Thomson Reuters—but Alan also shared his joy for product development as a key motive behind his continually lit entrepreneurial flame. As one might expect, Alan imparted several nuggets of advice on what to do when starting a company, but he also shared what he described as “near-death” experiences (for his companies) along the way.

Don’t mistake Alan’s mild-mannered delivery in our discussion for indifference to the outcome of his several companies; rather, in this interviewer’s opinion, it reflects his humility, peace with the process, and gratefulness for being afforded the ability to create at the highest levels. I hope you enjoy our conversation.

As usual, if you find this conversation helpful, please share with other aspiring entrepreneurs/company builders, and follow along as there are more stories to come.

Onward ~

Pete

2:06 -- Early Influences & Family Business

5:53 -- Transitioning family business to legal software company

12:03 -- Building Elite, Inc., the value of strategic partnerships and consultants

17:59 -- At approximately 150 employees, Elite is acquired by publicly traded Broadway & Seymour, which Elite later divest and operates independently.

23:55 -- Life after acquisition and new ventures, Chrome River

29:42 -- One key motive behind Alan's continued success and entrepreneurial drive

31:04 -- Facing challenges and near-death company experiences

36:04 -- Decision to raise capital 5 years in.

44:01 -- The difficulty in crossing the chasm from a company that sells to professional services customers to now one that also needs to sell to corporations; enter near death experience #2; ultimately succeeding and counting among its customers Cargill, Toyota, Liberty Mutual, etc.

51:26 -- How to overcome major competitors

54:11 -- Next company, Y Meadows, coming full circle and keeping it in the family!