Why I Started Advising Startups While Working a Full-Time Job

When I tell people that I work full-time at Microsoft, advise four startups, am building two of my own products, and mentor engineers on the side - the most common response is some version of “how do you manage that?” The honest answer is that the question assumes managing it is the hard part. The hard part was deciding to.

For a long time, I followed the traditional career model: one company, one identity, work hard and advance. It served me well for a while. Then I started noticing that the most energized, most curious, most effective people I respected didn’t work that way.

Why the portfolio career made sense for me

The full-time job gives me depth and credibility in a specific domain. The advisory work gives me breadth - I see five different companies’ problems in a month, which makes me a much better thinker about patterns. The products give me skin in the game as a builder, not just an advisor. The mentorship gives me clarity about what I actually believe by forcing me to explain it.

Each of these things makes me better at the others. That cross-pollination is the actual reason for doing it - not the financial diversification, not the resume building, but the compound interest on judgment.

A portfolio career is not about doing more things. It’s about finding the combination of things that makes each one more interesting than it would be alone.

What advising startups actually involves

Real advisory work - not the kind where you get a title and show up for the occasional review call - involves being available for the messy, in-between moments. The “our cloud bill just doubled and we don’t know why” message at 9pm. The “we’re thinking about pivoting the data architecture” slack. The “can I send you this deck before I send it to investors” request.

That’s the valuable part. Not the quarterly check-ins - the accumulated context and genuine relationship that lets you give real, specific advice instead of generic frameworks.

The practical constraints

• Be clear with your employer about what you do outside work - transparency prevents conflict later
• Pick advisory roles where you’re genuinely adding value, not just collecting the title
• Time-box the work - advisory should have natural boundaries or it expands into everything
• Don’t over-commit - two or three meaningful advisory relationships at a time is probably the realistic ceiling alongside full-time work
• Choose companies whose problems genuinely interest you - interest is what sustains quality advice over time

Who this model works for

Not everyone. The portfolio career requires a high tolerance for context switching, genuine interest in multiple domains, and the discipline to maintain quality across competing demands. It also requires having reached a level of seniority where your knowledge is worth paying for - early in a career, depth in one thing is usually more valuable.