Ask HN: What it is like to join a startup founded by serial entrepreneurs? | Hacker News Reader

Ask HN: What it is like to join a startup founded by serial entrepreneurs?

8 pointsmsoad3 comments

Have you worked for a startup founded by serial entrepreneurs that sold a couple of startups to big companies and started a new one with that money? Since they don't have funding issues it's a bit different. It's also different because founders execution capabilities are proven. What it is like to join such companies?

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It is very rewarding in the sense you can get multiple startups worth of advice. I've worked for two startups in the past several years, one with a CEO who had never sold (or scaled) a tech company. The other had a founding team with several acquisitions between them.

I heard many times "well something like this happened at XYZ company and this is what we did and it didn't or (or did work". Granted many problems are new with each venture, they all had a vast set of knowledge and startup experiences between them. I learned a lot by working with them and hearing their reasoning behind decisions.

Their network was also very, very strong as a result of having been around the block. This made for easy access to almost any company we needed to speak with.

It is also neat (and I learned the most) to be able to communicate on a very high level in all discussions. It was a totally different experience from the prior startup where I had to preface everything with a breakdown of the basics first (this is what SEO is and how it words).

It depends on the startup - my company was founded by serial entrepreneurs who created companies that sold for big acquisitions, but the founders still took on VC money a little later.

By the time I joined mine, the founders left - I don't presume the reasons, but the company is currently headed by a CEO with a passion in the space and the founders as advisors & board members. The company feels like any other startup I've been at, high pressure with products that at one point were dangerously close to failing without some herculean efforts to reverse technical debt, create a pathway to scalability, and timely releases of new products/features despite waterfall planning.

I have found that engineering gets the shaft, just like at most other companies. True leadership is appallingly missing, and heedlessly put companies at risk...but I digress.

I've had one client that was a serial founder, I think 3 companies already sold.

It was really different from working for "normal" first timers. He was much faster, more responsive and more likely to understand things like scope creep and technical challenges encountered ("more common sense" might describe it).

It was a real pleasure. I'll probably offer a discount to serial founders going forward...

NB: it might not mean the company "doesn't have funding issues". This founder (and many others I know) took external money because it makes sense financially. Park your savings in real estate and stocks, and take the much better terms investors will give you because of your track record. He was also quite careful with it.

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