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

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 takers that have endured along their journeys and found positive outcomes, with the hope of helping you find the best path for yourself.

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 ~