Ben Gilbert and David Rosenthal of Acquired – Lessons on Early Stage Investing and Getting Acquired – [Invest Like the Best, EP.196]

My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out.

In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David have learned across their careers. I hope you enjoy my conversation with Ben and David.

This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at

This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at

For more episodes go to

Sign up for the book club and new email newsletter called “Inside the Episode” at

Follow Patrick on Twitter at @patrick_oshag

Show Notes

(2:29) – (First question) – What they look for in new founders based on more experienced managers they’ve worked with

(5:07) – Difference between emerging vs legacy market

(9:17) – Research steps to determine if a market can get big enough to invest in

(12:08) – Working with other firms for doing an initial investment round

(15:42) – Recent trends in the supply of capital and number of founders in the VC space

(18:56) – Lessons they have learned studying corporate transactions

(24:13) – How do startups transform once they are acquired to increase their multiples so much

(28:10) – What they learned from deliberations that take place within the acquiring company

(30:39) – Most interesting deal for them to unpack

(32:44) – What are features of a business that is difficult for others to replicate

(35:52) – Any company that are intimidated to go up against

(37:37) – Who would they follow

            (38:52) – Blake Robbins Podcast Episode

(39:09) – Missing pieces in their skill set

(41:43) – Early green shoots

(44:40) – Lessons from Alaska Airlines acquisition and the value of scarcity

(47:07) – Kindest thing anyone has done for them

Learn More

For more episodes go to

Sign up for the book club and new email newsletter called “Inside the Episode” at

Follow Patrick on Twitter at @patrick_oshag