Hi, I'm Mike Innamorato.
Let me give you a little bit of my origin story, and no, sorry to say, I'm not Batman. First-gen. Son of immigrants. Computer science degree from SUNY Plattsburgh, a school nobody has ever called a target (no offense; I love all my Cardinals and that school). NYC-born and raised. Nobody handed me a network, a warm intro, or a map. That turned out to be the most important qualification for writing this newsletter.
Today's email is a 4 min read:
The path: banking, beer, insurance, asset management
Side Ventures
Why a career newsletter?
What you'll get, one post most weeks
Here's the path, so you can decide for yourself whether to take me seriously.
Out of school, I applied to more than 2,000 jobs and got zero offers. That story gets <link to that story> because what I learned digging out of that hole is the reason this newsletter exists.
The career that eventually happened did not follow anyone's playbook:
Banking. Product owner in legal operations at a national bank in Texas — my first real seat at the table, and proof that the way in doesn't have to look like the way you planned.
Beer & CPG. Chief of staff for Anheuser-Busch's new-ventures arm in New York, on the founding go-to-market team that scaled Nutrl and Cutwater to the #1 and #2 spirits-based canned cocktails in the U.S., inside a massive innovation portfolio.
Insurance. Technical product manager for AI at MetLife, where I took an AI risk assistant from pilot to 40,000+ employees.
Asset management. Today I work on legal AI at State Street, rolling out a contract intelligence AI platform and building products that save people time, money, and their sanity.
Along the way, I added an MBA from Johns Hopkins and a master's in entrepreneurship from Syracuse. Four industries, five functions, zero family connections used, because there were none to use. Every recruiter who called this path "unfocused" was describing the thing that now gets me hired.
SIDE VENTURES
Outside my 9-5 and weekends, I run The Civic Pulse — a nonpartisan "Government, explained. No spin." media company. A promise tracker that checks what politicians said against what they did, an agentic AI content pipeline, newsletters that ship on schedule, 30K+ monthly users, real paying subscribers. Built and operated by one person, launched for under $100, plus a new product in development…. You can read about how I launched that side hustle for practically nothing; the exact playbook is here →.
I'm telling you all this for one reason: everything I claim, you can click. I'm not a career coach with a framework and a Calendly link. I'm someone who does the work across domains, ships things you can inspect, and writes down what actually happens.
WHY A CAREER NEWSLETTER?
Because none of it came through the front door. The 2,000 applications taught me the front door is a pedigree filter, and every opportunity that actually changed my career came through a side door instead — a person, a project, a skill from one field that turned out to be rare in the next one. Once I saw the pattern, I couldn't unsee it.
WHY I'M ACTUALLY DOING THIS, IN DESCENDING ORDER OF NOBILITY:
I believe what I've learned can help people. Everything here is the advice I needed at 22 and couldn't find anywhere.
Spite. A meaningful percentage of this newsletter is powered by spite. Somewhere out there are 2,000 hiring managers who never wrote back, and every new subscriber is a small note to each of them. People underestimate spite — motivation quits on the bad days, but spite shows up early and stays late.
I'm tired of bad career advice. If one more person tells me to "just network," I'm going to network directly into the sea.
I'm tired of career advice from people who never had a hard part. If your origin story starts with Harvard or Wharton, A family friend at the firm, you're not writing for the 99% of us who started with neither.
People want to learn from someone real — not a guru, not a nepo hire with a podcast. Someone still in it, who remembers exactly what the rejection inbox felt like.
MOST CAREER ADVICE IS WRITTEN BY PEOPLE THE FRONT DOOR OPENED FOR. SIDEDOOR NEWS IS FOR EVERYONE ELSE.
WHAT YOU'LL GET, ONE POST MOST WEEKS:
Real stories of how people actually got in, the side door, not the cleaned-up LinkedIn version
My field notes from building alongside a 9-to-5
Tactical breakdowns: personal branding without a fancy title, building outside your 9-to-5, and the AI tools I use every day
The toolkit at CareerGeneralist.com — job boards, courses, and resources for generalist careers
BEEHIIV POLL
Where are you right now?
Deep in the application loop
Employed but restless
Building something on the side
Already through a side door
If you did everything right and the front door still didn't open, welcome. You're who this is for.
Say hi: hit reply and tell me where you are in your own search or build. I read everything, and reader stories become future posts.
