Entrepreneurship Exit Life Lessons Startups

I just sold my 5th tech startup. What should I do after going to Disneyland?

[published on Startup Grind]

Well, I actually didn’t sell the company but we sold the technology to another company. This type of transaction happens frequently because the acquiring party doesn’t want to pick up unforeseen liability. That said, what should I do now? Take the family to Disneyland is a given but after that, what next?

Exits can be the ultimate blank page.

Any exit — whether selling a tech company or leaving someone’s employ (planned or unplanned) — is an opportunity for growth and for many, anxiety. The good news is that no matter what the circumstance, it’s a blank page and we each get to decide what will be written on it.

This time, I’m hoping to leverage my entrepreneurial experience.

Perhaps by joining an existing team with exciting prospects. But after selling 5 startups, how does a guy get a “normal” job?


I did this once before when I sold my 2nd startup but it was an epic failure.

Back then, I contacted a few Venture Capital friends and asked if they had a portfolio company that could use a guy like me. (Yes, you can have VC buddies; especially if you never take their money.) Each seemed excited and so I visited with several companies. However, the CEOs of the two companies I found interesting worried that I had been sent by their money people to replace them (imagine that). Seriously, one said “you’d make a better CEO [blah blah blah]” and the other asked “should I be worried?”

So, I went on to found my next company. I interviewed myself and found that I was the right guy for the job!


So, here I am once again. Will things be different?

I don’t know. This time, I decided to send a private message to each of my first-degree connections on LinkedIn. More importantly, I chose not to screen whether I thought a particular connection might know of something for me. Here’s what I said:

“Hi [NAME],

[CUSTOM INTRO (short)]

I recently sold my 5th tech startup (now 5 for 5) and I’m looking to leverage my entrepreneurial experience by joining an existing team with exciting prospects that could use a guy like me. My experience is vast in technology evangelism, strategic marketing, and business development but I also have direct experience in many other areas (such is the life of a serial entrepreneur). I’m willing to relocate (domestic or international).

This is just an FYI… so don’t stress if you don’t know of an opportunity for me… it’s all good. I’m just casting a wide net. You never know where the next opportunity will come from. Attached is a copy of my resume.


PS If I can be of any assistance to you, please let me know. Oh, and if you haven’t seen my 4th installment of what’s #NotOnMyResume on LinkedIn, it’s out there now.”

The results.

Well, I sent out approx. 200 customized messages a day for several weeks. The replies fell into 4 categories:

  1. Thanks for sharing.” (This is one of LinkedIn’s automated response buttons… Microsoft AI at its best.) I would reply, “Don’t you just love those AI buttons? 😀” and frequently a real conversation would ensue.
  2. Hey, we see you recently had an exit and we’re looking for an investor (or investor partner).” Well, that’s not me. I explain that my interest is medical research towards a treatment or cure for my son (but that’s another story).
  3. We can’t afford a guy like you but perhaps you might give us your opinion on something.” I do my best here (I’m a big fan of giving back) but limit each appointment to 30 min or it swallows my day.
  4. Impressive resume… we might have something for you.” Yea! Then starts the mutual due diligence. Some of these “opportunities” are interesting… some are not.

I’m excited to get going on the next thing (that’s the entrepreneur in me) but I’m trying not to be in a hurry. Where one works and what one does is very important (to the individual and the family). Perhaps I’ll fractionalize my time and assist a number of these opportunities and see which bubbles to the top (in terms of mutual interest); then, dedicate myself to that. But, who knows and isn’t that great!

Today’s takeaways:

  1. Pursue every angle. No matter what part of your life, do absolutely everything you can. Only then can the universe kick in (whatever that means to you). One recent opportunity that came my way was the result of sending the message above to a PhD student in Texas. Had I taken the easier way and pared down my contact list to only those that I felt might know of something, I would have missed that one.
  2. Learn to connect; not just sell. If all you do is deliver a product (or service) and take their money… they’ll be your customer. But if you truly connect with people, they’ll be your customer and your friend. It’s better for them and it’s better for you. Which would you rather speak to? Which would be more forgiving? Which would do something without expecting anything in return? (BTW, this goes both ways.) Truly connecting is an art form.

Why not do my own thing again?

It’s not for a lack of ideas… entrepreneurs never have a lack of ideas. The fact is that for me the first 12–18 months of a startup are not what I love the most (e.g., form the company, identify the pain you’d like to solve, architect a solution). From the point in time that the solution is demonstrable until the end goal is reached (whether overall growth, acquisition, or IPO) that’s what I love!

As a side note…

I’ve often wondered if rather than assembling a team around a great idea, perhaps it would be better for entrepreneurs to assemble a great team and see what ideas come from that. Either way, wouldn’t it be just as satisfying to join a great team that’s properly funded? I think so but I really don’t know… I have no experience here. One thing is for sure… if it turns out not to be the case, I always have my mirror. 😀


Movie Quote:[Pete] Who elected you leader of this outfit? [Ulysses] Well, Pete, I thought the leader should be the one with the capacity for abstract thought, but if that doesn’t seem to be the case, hell, we’ll put it to a vote. [Pete] Suits me. I’m voting for yours truly. [Ulysses] Well I’m voting for yours truly too. [Delmar] Okay… I’m with you fellas.” — O Brother, Where Art Thou? (2000)

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