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  • Writer's pictureCory Cleveland


Updated: Nov 24, 2023

Jacob Koenig at The Insider's Guide to Finance

Jacob walks us through the process and considerations when looking to sell your business.

Selling your business is often an emotional and strenuous process, but it doesn’t always have to be. In today’s episode, special guest and expert closer, Jacob Koenig shows us how to navigate the complexities of selling a business and key considerations for business owners preparing for acquisition.

Jacob is a managing director and partner at Woodbridge International, a company that has specialized in helping clients sell their businesses for the past 30 years. His role and focus at the company is managing the sale process from bid through closing, acting as a trusted advisor for Woodbridge clients.

“Something we always say is, ‘Time kills deals. Time and surprises kill deals in particular.” — Jacob Koenig [0:09:05]

He joins us today to share valuable insights on selling a business and the process of bringing a sale to close. Together we explore key considerations for companies preparing for acquisition, why involving your management team early on adds value, how they build a market of potential buyers and why a competitive auction process sets them apart.

He touches on important factors and criteria of prospective buyers and the emotion versus logic component present from both sellers and buyers inherent in the process.

“[Selling a company] is not [always] all about money. Money is usually the number one driving factor but sometimes you’ll have an auction where there are multiple different buyers with similar evaluations and our client will go with one who has a lower evaluation but [is] more aligned with their view on how to grow their company going forward [and that] is more aligned with their view of how to keep employees on, motivated, or otherwise. But most importantly, who is going to actually have the money to do the deal they’re putting forth — the certainty to close.” — Jacob Koenig [0:28:51]

Finally, Jacob discusses his time spent working for Goldman Sachs in Asia, and the cultural nuances between American and Asian values and approach to business.

Join us for an exciting discussion as Jacob sheds light on the many elements integral to the sale of businesses, and international working culture. Thank you for tuning in.


  • A brief overview of his time working at Goldman Sachs.

  • His thoughts on the current state of the market.

  • Jacob’s perspective on the concept of ‘Picking up Pennies in Front of Steamrollers.’

  • He walks us through Woodbridge’s approach to buying and selling a business.

  • Levers of evaluation to look at to inch the multiple up or down.

  • Key considerations for you and your company in preparation for acquisition.

  • Why bringing your management team to meetings with buyers can add value.

  • Lessons to be learned from the phrase ‘Buyers are Liars’ according to Jacob.

  • We talk about time frames and the factors that influence them.

  • The steps of their process for preparing and selling a business.

  • Building the market of potential buyers and running a robust auction process.

  • Important factors and criteria of prospective buyers.

  • Emotion versus logic when selling a business deal to buyers.

  • His thoughts on buyers also bringing an emotional component to the table.

  • Advice to management teams prior to entering meetings.

  • The Japanese market and the challenges they are facing over there.

  • What it was like working in Taiwan.


Please note that the information contained in this interview is not financial advice but for entertainment purposes. I am not a financial advisor and make no warranties or representations concerning the accuracy or suitability of the information contained in this interview. I recommend that any and all investment decisions be made with the advice of registered investment advisors.


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