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 Woof16:54 -- Building a community and landing a product28:14 -- Leveraging micro influencers for brand growth30:25 -- Sales strategy: Amazon vs Direct Website Traffic38:28 -- Financing growth42:27 -- Utilizing AI in Business Operations44:27 -- 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 background7:47 -- First venture and learning experience10:51 -- Transitioning from corporate world to entrepreneurship, start-up capital (boot-strap)14:42 -- The birth of 10 Barrel Brewing23:02 -- The breakthrough! Hiring key talent32:23 -- Importance of mentors and learning to accept rejection from prospective investors37:05 -- 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, Pete1:00 -- Intro to Entrepreneurship and Failure4:02 -- Christa discovers entrepreneurism8:28 -- Founding of Fitlandia13:29 -- Did sticking to her values cost Christa her company?21:40 -- Learning from failure32:20 -- Next venture, building Cricket Fences41:33 -- Generational slides in mental health and awareness49:36 -- 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 mission12:15 -- Getting technical, navigating the speed of innovation within AI frameworks23:37 -- LLM vs SLMs, what's the difference? Why domain expertise is the winning ingredient30:54 -- The linear success path straight up to the right is rarely the case, how failures shaped his path to success35:21 -- 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!
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 company5:45 – Early influences and entrepreneurial spirit11:50 – Lessons from crisis management17:46 – Setbacks as a tech leader/lessons29:51 – Is it better to be “overcapitalized” or “undercapitalized”39:55 – Crisis Management Again!45:36 – Hyrdo Flask Journey: growth mindset59:45 – Navigating early crises and building company values1:02 – Scale challenges1:10 – Building a brand and advisory board1:19—When to develop leaders, and when not to1:22 – 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 experienced their dark or difficult hours, and Monica’s journey was no exception. We talked for an hour, but I could have easily spent a day with her unpacking the details of her journey. Hope you enjoy! ~Onward 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 remarks of 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? :) 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 Thanks again Monica for being an awesome guest! Stay tuned, more entrepreneurs and rule breakers to follow....
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 journey the ups and downs of entrepreneurism, including how to confront burn-out when one thinks they are immune to that possibility. Finally, she shares with us the most recent start-up she is joining as COO, Somos, somosxr.com, a company that unlocks the power of play to heal the brain and body, defining a new class of interactive rehabilitation and targeted therapeutics. Taylor has never waivered from her calling to work in company that not only build great technology, but that also promotes health and well-being. I was inspired. Also, I am terrible at marketing, but if you like what you hear and are learning please follow and share the pod. Let's help as many entrepreneurs as possible, also, my advertisers will appreciate it. Wait a minute, what advertisers? :) 1:05 -- Taylor's journey to entrepreneurship (let's just skip the Corporate America thing) 9:44 -- Embracing risk early in life 18:21 -- Lessons from failed VC funding 26:19 -- Burnout, recognizing and overcoming 33:45 -- Importance of core values in success 49:02 -- Transitions after an "exit" from the company 55:02 -- Innovative healing through technology Thanks again Taylor. More great guest to follow. Onward~
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 case, one can achieve balance and financial freedom. 1:29 -- Reynold's early career and drive to transition to entrepreneurship 8:02 -- Setting goals to achieve financial independence 11:39 -- From Corporate America to Real Estate, seeding the transition 20:52 -- Identifying a niche market - location, prop type, etc. 31:08 -- Solo Entrepreneur vs Team Dynamics; identifying what best suits you 44:23 -- Navigating set backs and failures in Real Estate Development 52:58 -- Developing a trustworthy financial model 100:02 -- Art of acquisition in business 105:14 -- Final thoughts and recommendations Onward!
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, etc.) and, if one can find complimentary skill sets he/she can be successful across a multitude of industries. Finally, since he's now seeding his next company, and deciding to take a more measured approach to solving a big problem -- enjoy. 1:26 --- Nick's Entrep Journey 4:49 -- Redefining Failure 13:36 -- The challenge of raising money in today's environment versus 2015--2019. 15:26 -- Today's VCs are out of touch with their role in the market, in part because they are getting squeezed by LPs. It was interesting to get a seasoned founder's perspective on the topic. 24:19 -- Bringing canned water to Mexico City. 30:39 -- I challenge Nick's decision to leave software industry and go into consumer packaged goods (but I like his answer:)). 44:59 -- Why Nick takes a pen and paper to every meeting 58:12 -- Most important character trait Nick identifies with that has made him successful: people
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 presence and over 25,000 employees, and as of September 2024 was the 250th most valuable company in the world by market cap. However, those circumstance didn’t stop Dan from following his dreams, as he jumped both feet in (let’s just say after the age of 45) to start ECFX in 2019 and not only managed to navigate his start-up through Covid, but five years later the company is growing quickly, has ~35 employees and millions in annual revenues. 2:52 -- Dan's entrepreneurial origins 6:47 -- Leap from corporate world, taking advice from mentors 12:20 -- Intrapreneurship doesn't always work 15:06 -- Raising money and managing expectations: "lighting a garbage can of money on fire" 21:16 -- Management style in today's employment market 30:13 -- Navigating the mid-stage cycle and journey now five (5) years in? What are the key aspects to balance now? What's the rule of 40? 51:12 -- What keeps you up at night, now that you are 5 (five) years in and have dodged the start-up cycle of death in first couple of years? 1:02 -- Perfect is the enemy of the good 1:05 -- Dan's top books for business owners
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 was inspiring, to say the least. While his military background proved valuable, especially, imho, as it applied to Kyle's mindset when starting a company, he also felt that the former special forces operators are under represented in the start-up world -- maybe a business opportunity? I hope you enjoy our discussion. Also, I am terrible at marketing, but if you like what you hear and are learning please follow and share the pod. Let's help as many entrepreneurs as possible, also, my advertisers will appreciate it. Wait a minute, what advertisers? :) 2:17 -- You never know where an idea will come from, an open minds = open doors 5:12 -- Nature vs. Nurture in Entrepreneurship 9:13 -- Military experience; father was in the Air Force; Kyle's path to joining the military and some key take-aways 23:35 -- What (30) days at a Fortune 500 company taught him 30:06 -- From Kyle's perspective, why planning has little value and why incremental goals might be more important 40:25 -- Applying Core Values to everything; the art of bootstrapping 42:38 -- The "unplanned exit" 44:46 -- One of Kyle's most important character traits for success 47:02 -- Biggest "Challenge" he faced as an entrepreneur 53:03 -- The right culture can save a company. Core Values from non-believer to believer 1:02 -- Closing with top three (3) traits to succeed Until next time. Onward!
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 the young age of fifteen (15) when he founded a web services company that helped finance his college education. Everyone can expect to be aided by luck and perhaps unknown forces in their journeys, Gabe shares how a chance encounter lead to his employment at MIT/Lincoln Labs and ultimately how he transitioned to start his own consulting company. What I recognized in Gabe as a superpower was knowing when to "pivot," can elevate not only one's chances of longevity, but that ultimately it might be necessary to a successful outcome. 2:01 -- Gabe's origins of entrepreneurism 5:25 -- Learning the value of "boostrapping" at a young age 8:22 -- Roam Devices, Gabe's latest endeavor. Importance of adoption at any stage of a business. 13:10 -- Why we all should pay attention to "chance" encounters. 20:00-- Humble beginnings. Bootstrapping to success. How to de-risk a shift from core business. 25:34 -- When to pivot. 30:45 -- Leveraging Customers to finance your idea (self-funding and building goodwill with customers). 47:42 --- Challenge of selling hardware products. 58:24 -- Importance of nailing "culture" 104:11 -- When getting acquired is "not" on the radar, but recognizing "timing" is everything as Apricity is acquired in 2021. 119:12 --- Gabe's top traits for success
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 couple of years suffered a serious physical injury while hunting that has sent him searching for recovery, purpose and balance again. An episode that touches on more than just being an entrepreneur, but how "life" has a way of interfering with our plans, and sometimes dramatically so. In "Bold" are the my favorite take-away sections. 2:07 --- Transitioning from RE Entrepreneur to Tech Exec Career at Oracle 5:22 -- Entrepreneurial Spirt at Oracle & Dot-Com Boom 10:47 -- Different flavors of entrepreneurship: intra, extra and the classic entrepreneur. -- embracing constant change; how Oracle fosters 23:49 --- "Drive & Center" and the Rubber Band Theory 40:41 --- Self-discipline as "core" tenant to life success. The importance of getting after it early in life. 52:50 -- Leadership and continuous learning 1:03 --- Leaving Oracle for a Start-Up (timing) and a successful exit 1:08 --- A tragic accident and life changing injury 1:10 -- In the middle of finding purpose and the daily "grit" to overcome adversity
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 successfully acquired 7 years later, he's now onto start-up 3 and 4. It sounds risky, and it was, but one of my main takeaways today was how Justin "de-risked" his launch into the start-up world. Hope you enjoy and find value learning from his journey. 1:54 --- How one editorial on start-ups stuck with Justin 15 years later. We never know where that source of inspiration will come from. You'll have to listen to find out the article! 4:47 -- 7 years at professional services firm (Frank Russell Company), with an office view and one year away from a paid sabbatical. Why leave now? 6:49 -- Product Market Fit, attaining the "fit" before leaving his job. Acquiring an entrepreneurial spirit -- trading domain names to pay for Grad School. 12:11 -- Importance of Customer Validation not just on price, but product and supporting services. 28:52 -- Importance of seeking advice and filtering it. 37:32 -- Justin's biggest challenge (and failure) along the way. 49:01 -- Identifying and leveraging your superpower. 53:11 -- Importance of planning an "exit" strategy. Contrary to popular opinion. 1:09 -- The exit cycle, what it looks like. I'd like to take a deeper dive on this point another time, we just scratched the surface today. 1:18 -- Celebrating success. Justin's next start-up and how he's more focused now, and still enjoys the process. I'll be taking a bit longer break (than every two weeks) until our next session, week of July 8th and have a guest lined up you will not want to miss. Onward ~
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, Ian is a great story teller and imparts many valuable lessons if you are an aspiring entrepreneur in any industry. 3:23 -- The beginnings, Ian's foray into a burgeoning pizza chain. The accidental entrepreneur. 9:54 -- Biggest challenge to launching a restaurant brand. 22:51 -- Success factors for a restaurant; seed capital, mentors and being in the "Path of Progress" 29:05 -- Financing a restaurant venture that's growing 47:30 -- Finding the ideal partner and passion 56:00 -- Starting a restaurant in a recession, 2008, and later the value of strategic financing; role of private equity 1:10 -- Importance of being an "Editor in Retail." Ian explains how simplicity and focus are integral to execution at scale 1:15 -- Exiting Lemonade (timing) and how his experiences prepared Ian and his partners to transition to the manufacturing/production side of the business. This aspect reminded me of Bayard Fox's journey to the founding of Cement Elegance (from retail to production) 1:30 -- Some key takeaways. Join us in a couple of weeks as we interview our next successful entrepreneur, and please pass along the pod to others if you like what you are hearing. Onward ~
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 definition of an entrepreneur? 4:17 -- Main takeaways from previous interviews 11:16 -- Patterns and traits of successful entrepreneurs 23:01 -- Why optimism matters 31:52 -- Are entrepreneurs more happy that non-entrepreneurs (employees), generally speaking? 36:25 -- A downside to entrepreneurship 43:51 -- Balance of optimism vs rationality 52:51 -- Role of craziness for entrepreneurs Next week: join guest and co-host, Chris Capdevila, who was a guest the other week, and, the gentlemen that sold his company to Oracle, as we dialogue with Ian Olsen, co-founder of a large restaurant chain, that was ultimately financed by Blackrock, a PE firm. Learn about his journey, as well as what he's up to now. Eric is off rafting for the week!