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

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

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

This will be our last episode for 2024, marking the

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.

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

We are excited to have Dan share his story on the Bending

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

Don’t mistake Alan’s mild-mannered delivery in our

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!

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 executive, where he spent most of his professionalcareer, was relevant to Hydro Flask’s success, if not an advantage in running a consumer product company. In March 2016, Helen of Troy Limited purchased HydroFlask for $210 million.

Scott Allan retired in March 2020, stating, "The goals that I initially aspired to accomplish have largely been achieved.” He continues to be active in advising and investing, with a particular emphasis on consumer brands and outdoor-oriented products and services.

I hope you enjoy the interview. Thanks again, Scott, for taking the time to give back and share your journey.

As a reminder, I am terrible at marketing, but if you like what you hear and are learning please follow and share the pod. I am now also making content available on a youtube channel (Bending Rules) where “shorts” will be shared to codify some of the instructive remarksof pod guest, if one is not inclined to listen to a whole episode😊.  Let's help as many entrepreneurs as possible, also, my advertisers will appreciate it. Wait a minute, what advertisers? :)

Onward ~

2:54 – Transition from technology companies to consumer product company

5:45 – Early influences and entrepreneurial spirit

11:50 – Lessons from crisis management

17:46 – Setbacks as a tech leader/lessons

29:51 – Is it better to be “overcapitalized” or “undercapitalized”

39:55 – Crisis Management Again!

45:36 – Hyrdo Flask Journey: growth mindset

59:45 – Navigating early crises and building company values

1:02 – Scale challenges

1:10 – Building a brand and advisory board

1:19—When to develop leaders, and when not to

1:22 – Ongoing contributions to outdoor community brands and products

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 strategic buyer in 2023. Well, Monica Enand did just that, all while growing the company she founded, Zapproved, to approximately 170 employees, earning recognition more than once as one of the top 100 companies to work for in Oregon, and leading the company as CEO over a sixteen-year time horizon.

Having met Monica over 15 years ago when she was running Zapproved in its early days from a small office in Portland, OR, I was excited that she was inclined to share her story on the Bending Rules Pod. Since I was already impressed with Monica’s journey from afar, it was yet another lesson in perseverance, grit, and belief in oneself. I was also reminded that most entrepreneurs, regardless of how overtly successful they have become, have

We talked for an hour, but I could have easily spent a day

As a reminder, I am terrible at marketing, but if you like what you hear and are learning please follow and share the pod.  I am now also making content available on a youtube channel (Bending Rules) where “shorts” will be

2:16 -- Zapproved Journey and Origins of entrepreneurism

12:53 -- No domain experience, finding a product niche

14:12 -- Get out the credit card, early days of financing

22:59 -- Moment of Truth. Am I going to have to shut this down? Where she found support

26:14 -- Raising capital in tough market (no financing for 5 years)

30:01 -- Wait a second now investors like us? Navigating PE relationships and deciding on a partner

40:07 -- Getting knocked down and journey to build a world class culture

48:40 -- Importance of networking your entire journey

55:25 -- Overcoming gender bias

59:12 -- Everyone needs to get lucky along the way, Monica shares one story

1:04 -- Parting advice for entrepreneurs

Stay tuned, more entrepreneurs and rule breakers to follow....