JACOB TALLY
FINANCIAL ADVISOR
A Pattern
At 18, I left Texas for a tiny, unconventional college in Switzerland that nobody had heard of. I got to see the world and earn a degree at the same time. At 30, I left a stable, well paid finance job at a Fortune 500 chemicals company to move to Seattle for... I wasn't sure what, exactly. But I landed at one of the fastest growing consumer startups of the 2010’s. Four years later, I left that to join the cofounders of a DTC meat company startup as their first employee, stepping in literal cow sh*t. But we went on to grow 20X and successfully raised Series A and B investment rounds. My career grew and scaled with the company.
Each time, the "sensible" path was obvious. Each time, I chose the other one. I bet on myself.
If you're reading this page, you may be considering a change of your own. Perhaps you've accumulated something (e.g., equity, experience, a title) and you're wondering whether you have enough runway to do something different. Stuck in your own success, and ready for something new and unfamiliar.
Familiar Ground
I help startup and tech professionals figure out if they can afford to take the leap, whatever that may be. For some, it might be work-optional by 50. For others, it’s devoting time and resources to a cause they care about. Perhaps it’s something more specific though, like unwinding a concentrated position that’s 40% of their net worth that they’re losing sleep over.
After 10+ years at VC-backed startups in the Seattle area, I’ve seen the ups and the downs.
I've navigated the full spectrum of equity compensation: early-stage options, RSUs that vest quarterly, and liquidity events. I've also had to fire people, survived layoffs and mergers, and seen what happens when the growth story stops working. That context matters when connecting with clients navigating similar circumstances.
And it helps me do one thing: turn my clients’ uncertainty into an informed decision.
What I’m Building
I spent 15 years at startups chasing ambitious growth targets that often had no basis in reality. Huge objectives, no real plan, everyone sprinting toward a number that moved every quarter. Some of those bets paid off. Most did not.
Launching a financial planning practice has been a breath of fresh air in that regard. I’m building something deliberate, intentional, and centered on personal relationships. Something that I truly enjoy and can continue to do for another 20 or 30 years.
Most advisors want a book of 100+ clients. I'm targeting a fraction of that. People who care about the long term, who will be engaged in the process, and who aren't looking for someone to rubber-stamp decisions they've already made. This has to be mutual. I'm selective about fit, and you should be too.
The Boilerplate Stuff
Most advisor bios talk about credentials and a passion for helping clients achieve their dreams. The latter is tablestakes, and I’ll be quick about the former.
I earned my Series 65 license in 2024 and joined Prospero Wealth in early 2025. But following markets, building financial models, constructing portfolios and analyzing investments are all things I've been doing for 20+ years. In fact, my first job out of college was 2 years spent serving clients at Fidelity Investments, so you might say that my career has come full circle.
Let's Connect
If you work at a startup or tech company, and have equity comp you're not sure what to do with, or if you’re wondering whether your financial situation gives you more options than you realize, then let’s chat.
