[hn-VZ4N8hcYCjKw]

I took a sabbatical after my dotcom imploded in 2000.

Huge, huge mistake.

When I tried "returning" I was either too corporate for startups and too startup-y for large organizations. I was both too young for roles I had already filled and too old for technical roles I was interested in.

I bounced through a series of startups, averaging less than a year before leaving.

I tried consulting but could never command the rates that would make it worthwhile.

I tried my hand at my own startup and failed miserably. I did not have the business sense, could not find a partner, and failed to convince a single investor to invest.

I suck at business and organizational politics.

I fell into the role I had in the 1990s which gave me some brief status and minor wealth, but was too busy firefighting then to learn how to leverage that into a better role.

While I believe I excel at managing stuff: people, projects, technology, it is hard to convey that in an interview.

Eventually I said fuck it.

I stopped applying for the CTO and I/T management roles I was interested in.

I told recruiters I am retired, but this had adverse side-effects I did not expect. I now reply that I am not interested in whatever role they are offering this week.

I used the knowledge and experience I have to switch to investing full time, now about a 50-50 mix of publicly traded stocks and startups in various stages of success/failure.

I mentor students in local bootcamps and try to help them find jobs after graduation.

I am still deeply technical, I throw together mock services and run them on different platforms to see what works, what fails and use that to guide my investments. I play with things like containers and IoT crap at home to keep current.

I hang out here to learn what the new hotness is (both what HN thinks it is, and what is coming in from the edges).

I learn a lot from the great writers here like patio11 and tptacek and others.

What startups have up and coming personnel to track? Which startups have people to avoid? I definitely check out founders and lead technical staff of the startups I invest in. If someone is a jerk here, they are unlikely to be someone I want to invest in.

I do not know if any of this counts as "leaving I/T" or not.

[mailshanx]

Would love to hear more about your experiences, both at various startups as well as job hunting. What are some of the more memorable startup experiences you have had? What kind of roles did you try applying for, and how did recruiters / hiring managers react?

[hn-VZ4N8hcYCjKw]

Roles: mostly management or CTO. Usually, but not always, recruited by the management team, but bounced in the early stages of the process.

Most memorable was being told I was unqualified for a role because I did not clearly whiteboard how to use some aspect of the Spring Framework. Memorable because: the company did not use Java. At all. Was a RoR shop.

Another time I was recruited to step in as an "emergency" CTO, like, could I start Monday (this was the preceding Wednesday) because the technology team was melting down under the current CTO. One catch: they wanted the current CTO to interview me to get his opinion. You can guess how well that went.

I did not pitch myself as a hardcore techie and did not apply for roles which appeared to be hardcore technical roles. The CTO roles I interviewed for were really CIO roles, management, process, that sort of thing, with some technical awareness. But what I find is companies want to hire hard core technical people for these roles, and then have a mutual miserable experience as they learn that knowing everything there is to know about the latest whizbang framework does not necessarily guarantee that person will be great at hiring, managing people and process and projects or negotiating the growth of the organization. Sure, there are hardcore technical CTO roles, but I mostly avoided those. And not so much because I didn't know the technical aspects, but it's not where my strengths are.

I find companies avoid hiring managers as managers, in either startups or large organizations. They seem to prefer promoting their senior most technical people into management, even at the expense of that person's technical skills atrophying while they stumble through learning how to manage people or projects or products or whatever.

And you know, peace. This is how people think technology organizations should operate. Not my job to fix technology recruiting or personnel management.

[employee8000]

Why did you bounce through a series of startups?

[hn-VZ4N8hcYCjKw]

Various reasons, most common was that I would be recruited for one role, and within a short amount of time after starting the role would radically shift to become a role I was either unsuited for, or excruciatingly overqualified for. Don't recruit senior staff to run through change lists. Don't hire someone for one role and then radically change the role after they start working for you. One time I was hired to build a group fulfilling a function, simultaneously the budget for the department was zeroed out and all headcount dispersed to other departments.