// JACOB TALLY · FINANCIAL ADVISOR
Can you afford to make your move?
I've left the stable path several times to bet on myself and start something new.
Now I help clients run the numbers and pursue their own goals.
Whatever the move is — I help you determine if it’s within reach.
SEATTLE, WA
// A PATTERN
Choosing the unfamiliar path
01
Three times, the sensible choice was obvious. Three times, I chose the other one.
At 18, I left Texas for a tiny, unconventional college in Switzerland that nobody had heard of — and saw the world while earning a degree. At 30, I left a stable, well-paid finance job at a Fortune 500 company to move to Seattle for… I wasn’t exactly sure what. I landed at one of the fastest-growing consumer startups of the 2010s.
Four years later, I left that to join the co-founders of a DTC meat company as their first employee — stepping in literal cow sh*t. We grew 20X and raised multiple rounds of VC capital. My career 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 on this page, you may be weighing a move of your own. Maybe you’ve built something you feel anchored to — equity, experience, a title — and you’re wondering whether you have the runway to do something different. Stuck in your own success, and ready for something new.
// WHAT I DO
I turn big “what if’s” into informed decisions
02
I help people figure out whether they can afford to make a change — whatever that change may be.
For some, the move is being work-optional by 50. For others, it’s redirecting time and money toward a cause they care about. Sometimes it’s more specific:
Equity compensation. Early-stage options, RSUs that vest every quarter, and what to do when a liquidity event finally arrives.
A concentrated position. A single stock that’s grown to 40% of your net worth and is costing you sleep.
A career pivot. Leaving a sure thing for something that might be better — and wanting to know the numbers first.
After 10+ years at VC-backed startups in Seattle, I’ve seen the ups and the downs. I’ve navigated the full spectrum of equity comp myself. I’ve also survived layoffs and mergers, had to let people go, and watched what happens when the growth story stops working. That context matters when I’m sitting across from someone navigating the same thing.
10+ years
inside VC-backed startups, through the ups and the downs, fundraises and failures
20X
topline growth as the marketing leader (and first employee) of a Madrona-backed DTC startup
20+ yrs
following markets, building financial models, and constructing portfolios
// WHAT I’M BUILDING
A small practice, built to last
03
I’m building a deliberate, intentional practice centered on a handful of real relationships — not a high-volume book.
I spent 15 years 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. Launching a financial planning practice has been a breath of fresh air — something I can genuinely enjoy and keep doing for another 20 or 30 years.
Engagements are two-way. I’m selective about fit, and you should be too.
The usual model
100+ clients, lightly served
A large book where most relationships are transactional and the plan gets a rubber stamp once a year.
How I work
A fraction of that, deeply served
People who care about the long term, stay engaged in the process, and want a thinking partner — not someone to approve decisions they’ve already made.
// THE CREDENTIALS
The résumé — I’ll be quick
04
Most bios lead with credentials and a passion for helping clients reach their dreams. The second is table stakes. Here’s the first, briefly.
I started at Fidelity Investments in 2004. I was 20, and it was my first job out of college. After 2 years there, I took a detour. I got my MBA, spent a few years in finance at a Fortune 500 company, and then a decade in start-ups. I earned my Series 65 license in 2024 and joined Prospero Wealth in early 2025. I passed the CFP® examination in November 2025 and am completing the experience requirement before I can officially use the marks.
Following markets, building financial models, constructing portfolios, and analyzing investments are things I’ve done for 20+ years. I have first hand experience with equity comp and M&A. Looking back at that first job at Fidelity Investments, my career has come full circle.
You might have more options than you think.
If you work at a startup or tech company with equity you’re not sure what to do with — or you’re just wondering whether your situation gives you more room to move — let’s talk. One conversation, no pressure.
// COMMON QUESTIONS
A few things people ask first
Who does Jacob Tally work with?
I work with startup and tech professionals — and others weighing a significant financial decision — who want to know whether they can afford to make a change, such as going work-optional, managing equity compensation, or unwinding a concentrated stock position.
What does Jacob Tally specialize in?
My focus areas include equity compensation planning (options, RSUs, and liquidity events), concentrated stock positions, and work-optional and career-transition planning for people in startups and tech.
Is Prospero Wealth a fiduciary, fee-only firm?
Prospero Wealth is a fee-only investment adviser registered with the SEC and acts as a fiduciary for its clients.
How do I start working with Jacob?
The first step is a no-pressure consultation. You can schedule a call on my calendar or send me a message on LinkedIn, and we’ll figure out together whether it’s a good mutual fit.
