Ep. 12 — The Personal Trainer for Your Business Exit with JT Kraai

by | Feb 7, 2023

Welcome to the “Show Me The Way” podcast with David Seitter

In this episode of Show Me The Way,” Dave sits down with JT Kraai from Exit Strategies 360, to discuss the personal process of selling a business, whether to retire after selling your business, and maintaining realistic expectations throughout the process.

Ep. 12 — The Personal Trainer for Your Business Exit with JT Kraai

Introducing JT Kraai and Exit Strategies 360

Dave begins by explaining why he asked JT to join him on the show, and then asks JT to introduce himself and give a little bit of background.

  • JT discusses his background, including multiple moves around the Western U.S.
  • He notes that regardless of where he is living, he is able to help coach clients through their business exit strategies.
  • He then explains why he began his company over 20 years ago.

Dave asks what his general business model looks like in helping people go through the process of selling their business.

  • JT begins by stating that he goes in without an agenda, but rather wants to educate and prepare people for what the process to sell a business is going to hold.
  • After prompting from Dave, JT goes into detail about his process with clients, including asking questions about reasoning, timing, etc.
  • He says that many times people come in without knowing what to ask, which he helps by walking them through the process of selling a business.

The Personal Process of Selling a Business

Dave asks how long it takes for him to complete this part of the process with a client.

  • JT says it’s fully dependent on the business owner and what steps they have already taken.
  • He then explains how some come in with all of the numbers ready to go, while others he helps gather the necessary info in order to properly value their business.
  • He mentions some variables that can drive certain styles of business sale, any other key factors that make a business unsellable until they are cleaned up.
  • Following further questions from Dave, JT says that he focuses on companies that are worth between $5 million to $100 million.
  • JT says that sales of businesses can take many different forms from partnership buyouts, to kids or key employees purchasing it, dissolutions, going to market, selling to competitors, etc.

Dave says this is why he calls JT a personal business trainer, because he helps guide people to get their business to the next level so they can engage in a succession plan that works for them.

  • JT agrees that it is very hands on, and that selling a business is a very emotional thing with lots of forethought put into it.
  • He discusses how different the timelines are depending on where people are at, as well as different deal structures that can help people get more money in their pocket through the sale of their business.

Dave asks JT for intriguing stories, either good or bad, that he has seen over his years of helping sell businesses.

  • JT first recalls a horror story about a client that ended up causing the deal to fall through.
  • He then discusses some things that he considers huge successes when helping people sell business.
  • He also mentions a phone call he got after helping someone sell their business and enter retirement.

Selling a Business and Retiring or Not

Dave follows this line of thinking about retirement and asks JT if he does any coaching for clients around what comes after selling their business.

  • JT says he does do a little bit of coaching, and then mentions another strategy that is becoming more and more common that he calls a “half step” towards retirement.
  • He discusses what this looks like and how it can help people transition, which Dave agrees with and responds to.
  • He then dives into the importance of managing the company culture during the transition phase.

Dave asks JT for his top key lessons for someone who is thinking about selling their business.

  • JT says that if he’s talking about clients, his biggest lesson is to ask the uncomfortable questions, and explains why.
  • He then continues by explaining how important it is to really know the numbers, and how it can end up with more money in your pocket.

Realistic Expectations of Selling a Business

Continuing along the same line of thinking, Dave questions JT how long people should expect between an LOI and sale of a business.

  • He notes that while many people say 90 days or less, it is often 4-5 months.
  • JT adds that if someone just walks in the door and needs help getting all the pieces together, to expect the whole process to take anywhere between 10-14 months.

Dave asks how JT deals with existing professionals that a company has been working with for years.

  • JT explains how he begins by asking questions, and when he pushes back on their answers versus when he lets them continue on unhindered.
  • He then mentions when he will recommend to bring in outside professionals.


To get a hold of JT Kraai he says to contact him via email, LinkedIn, or his website.


To reach out to Dave for advice or consultation, please visit www.davidseitter.com or email him at dseitter@spencerfane.com



This podcast is provided for educational purposes. It does not constitute legal advice and is not intended to establish an attorney-client relationship. The recommendations contained in this podcast are not necessarily appropriate for every individual or business. In determining the best course of action, business owners should consult with an attorney on their distinct circumstances.