Transitions

My guest today is Mike Botkin, the CEO at OneOutdoor Holdings, a private investment company. Mike's had a fascinating journey so far with a career that spans everything from being a state championship-winning high school basketball coach to COO at a diversified family office holding company to architect of a successful roll-up of commercial landscaping businesses in the Southeast, all before the age of 34. In this episode we discuss Mike's ability to overcome challenges, his unflinching belief in himself and his ability to solve problems, and how he views and manages risk.

Mike Botkin:

Mike on X

OneOutdoor Holdings

Tim Ludwig:

Tim on X

Podcast website

Topics:

(00:00:00) - Intro

(00:01:25) - Moving 13 times as a kid

(00:06:32) - Can you teach someone to ‘have that dog in them’ or is adversity required?

(00:08:45) - What did the future look like for you coming to the end of high school?

(00:19:14) - Following a probability outcome-driven life

(00:24:32) - Mike’s early career

(00:31:17) - Finding fulfillment

(00:34:22) - Being a contrarian thinker

(00:40:05) - Mike’s post-teaching career

(00:51:38) - The power of a supportive spouse

(00:57:18) - The business Mike bought and his evolution as a manager

(01:08:24) - Selling the business

(01:12:52) - Advice for listeners

The content of this podcast does not constitute investment advice, an offer to provide investment advisory services, or an offer to sell or solicitation of an offer to buy an interest in any investment fund.

Transitions with Tim Ludwig is produced by Johnny Podcasts

My guest today is A.J. Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management where he teaches multiple classes on the topics of entrepreneurship through acquisition and small company leadership.

A.J. previously was the president of Onesource Water, the third-largest bottleless water service business in the U.S. and the founder and CEO of ArchivesOne, the third-largest records management company in the U.S., which he sold to Iron Mountain after 17 years of operation. Among the topics we discuss in this episode are looking at life in thirds, the importance of protecting your time, and what it felt like to sell the company he founded. 

A.J. Wasserstein:

Case Studies at Yale

A.J.'s book: What Matters Most

Tim Ludwig:

Tim on X

Podcast website

Topics:

(00:00:00) - Intro

(00:02:05) - Dividing your life into thirds

(00:07:02) - AJ’s first third of life

(00:10:38) - AJ’s second third of life

(00:16:36) - How has your idea of leadership evolved over your career?

(00:24:56) - The experience of selling a business you founded

(00:38:16) - Becoming an empty nester

(00:46:52) - AJ’s Third third of life

The content of this podcast does not constitute investment advice, an offer to provide investment advisory services, or an offer to sell or solicitation of an offer to buy an interest in any investment fund.

Transitions with Tim Ludwig is produced by Johnny Podcasts

My guest today is Moses Kagan, the Co-founder at Adaptive Realty, founder of Re-convene, a leading real estate private equity un-conference, and partner at ReSeed, which has been described as Y Combinator for real estate sponsors. Moses has a fascinating background and some of what we discuss in this episode includes how self-advocacy and competitiveness influenced his path in education and business, his journey to a successful real estate career, and the role of mentors in life and business.

Moses Kagan online:

Moses on X

Adaptive Realty

Re-convene 2024

More from Moses

Tim Ludwig:

Tim on X

Podcast website

Topics:

(00:00:00) - Intro

(00:01:33) - Moses’ family history and his upbringing 

(00:26:22) - Moses’ early career & Real Estate

(00:40:23) - The power of writing publicly

(00:46:54) - The perception of Moses on ReTwit & the difficulty of entrepreneurship

(00:57:13) - Pivotal moments for Moses’ business

(01:05:57) - Moses’ next chapter

(01:08:42) - Teaching vs. Mentors

The content of this podcast does not constitute investment advice, an offer to provide investment advisory services, or an offer to sell or solicitation of an offer to buy an interest in any investment fund.

Transitions with Tim Ludwig is produced by Johnny Podcasts