Before I die, I have a whole bucket list I want to get through. One item is experiencing what it’s like to be a startup employee whose company goes public. If you’re considering joining a startup, or already at one waiting for your lockup to expire, this post is for you.
I spent 13 years in banking helping companies go public. I saw the champagne, the headlines, the overnight multi-millionaires. But I never truly understood what it felt like to be on the inside, until now.
That finally changed on March 19, 2026, when the Fundrise Innovation Fund, VCX, listed on the NYSE. For the first time, I understand what it feels like to hold potentially life-changing money that’s locked up for six months. The experience has also taught me a new dimension of investor psychology I couldn’t have learned any other way.
I’ve waited four months to publish this post to let the initial listing mania die down and give myself time to reflect. After investing since 1996 and working on IPOs from 1999 to 2012, I’ve learned that acting on investing FOMO is generally detrimental to building wealth. Better to write with a clear head than a euphoric one.
The Goal I Could Never Quite Reach
When I left finance in 2012, I wanted the full startup experience. I lived in San Francisco, after all, the startup capital of the world. I applied to Airbnb at a $3 billion valuation, then to Uber when it was still scrappy. No luck.
So I did the next best thing. I invested in every public tech company that said no. I then put money into traditional venture capital funds for private company exposure. If I could not sit at their table, at least their employees would be working to grow my capital.
But the curiosity never left. From 2013 to 2015, I consulted part time with Empower (previously Personal Capital) and got a taste of startup energy. The equity I received 3.5Xed after Empower acquired Personal Capital years later. Not life-changing money, and not an IPO, but enough to confirm that I enjoyed startup culture.
After that I traveled with my wife following her creative severance negotiation in 2015, then spent six years fully immersed in fatherhood starting in 2017. In late 2023, the itch came back. A VC friend connected me with a fintech company at the Series Seed stage, and I gave it four months. Good people, but not the growth trajectory and fit I was looking for. Ultimately, the company was acquihired, so no IPO there either.
I kept searching for the feeling I could not name.
Had The Best Startup Job All Along. I Just Did Not Know It.
When Fundrise’s VCX listed and I watched the share price move in real time, something clicked.
I have been working with Fundrise as an affiliate partner and user since 2016. What started as a genuine search for real estate diversification into the heartland and away from expensive San Francisco property turned into one of the most enduring professional relationships of my post-finance life.
I developed the BURL framework (Buy Utility, Rent Luxury), which argues for investing in lower-cost areas of the country for greater income while renting in high-cost areas due to low cap rates and better relative value. Fundrise became both a subject I wrote about deeply and a sponsor of Financial Samurai.
For a decade, that relationship produced consistent sponsorship revenue that I reinvested back into this platform to keep it free and my own Fundrise positions. I was not just an affiliate. I was a believer. When commercial real estate got hit starting in 2022 as the Fed hiked aggressively, I did not walk away. I kept writing, kept analyzing, kept being honest about both the challenges and the long-term thesis.
That loyalty ran both ways. Fundrise kept investing in the relationship too. Today, Fundrise manages over $3 billion in residential and industrial real estate, plus a $1.5+ billion publicly listed venture fund anybody can buy and sell.
Watching the VCX listing unfold, reading the coverage, seeing the investor reaction, I felt something I never felt watching an IPO from a trading desk.
Then it hit me.
Think about what a startup employee actually signs up for. In exchange for equity that might be worth something someday, you commit your time, your energy, and years of your career. You report to a boss. Sit through morning standups. Grind toward KPIs, manage people, and travel when the company needs you to.
It’s demanding work and the potential equity upside is what makes the sacrifice worth it. Somewhere along the way, without realizing it, I ended up with a version of the upside without having to make the same trade.
As Fundrise’s long-time partner and investor across their products, I benefit when Fundrise does well, similar to an employee with equity. But my “job” is simply to do what I would do anyway: research, analyze, and write about investments I actually own.
Meanwhile, I have no meetings, no KPIs, no direct reports, and no business travel. I got to spend the last decade raising my two kids and playing pickleball at 10 am on Tuesdays. That’s a pretty good gig!
None of this would mean much without Fundrise executing on their end. The VCX listing on the NYSE took years of planning and building to pull off.
I remember talking with Ben Miller, Fundrise’s CEO, during COVID about his idea to launch a public venture product. Plenty of people told him it couldn’t be done. But after watching him democratize access to real estate investing since 2012, I was enthusiastic he could do the same for venture capital.
I never got the Airbnb or Uber offer. It turns out I got something arguably better: startup upside without giving up the freedom I retired to find.
What The 6-Month Lockup Actually Feels Like
If you have never been through a lockup period, let me try to describe it accurately. This is technically my first one. I joined Goldman Sachs two months after it went public in May 1999, and Credit Suisse was already public when I hopped over.
You have shares. The shares have a price. That price represents a number that could change your life in concrete, specific ways. And you cannot touch any of it, usually for six months.
Every morning you check the price. You do math in your head. You catch yourself designing a future that does not exist yet. Then you remind yourself that none of it is real until the lockup expires, and you go about your day carrying this strange financial suspense in the background of everything.
But you cannot help dreaming about what you could do with the proceeds. I have been a big dreamer since I was a kid. Dreaming is free, so why not dream big? You never know what might happen, and an optimistic attitude tends to pay dividends in life, relationships, investing, career, and family.
I remember one evening in 1999, leaving the office at 9pm after arriving at 5:30am, dreaming about retiring by 40. That dream turned into a game plan, which turned into a negotiated severance that let me leave six years ahead of schedule. Dreams have a funny way of becoming blueprints.
Post-listing, here are some of the things I’ve caught myself dreaming about:
- Superfund 529 plans for grandchildren I do not have yet
- Take my parents on a true around-the-world luxury cruise, the kind they would never book for themselves
- Write a six-figure check to the Pomeroy Center, which serves people with disabilities
- Write a six-figure check to my children’s school to help build out the grounds and provide more tuition support for families
- Pay off the remaining mortgage on a rental property I have owned since 2014, which has a 7/1 ARM expiring in December 2026, three months after the lockup window opens
- Buy an estate in Kahala, Honolulu, a block from the beach to be closer to my parents
- No longer feeling any strain about paying for independent grade school tuition
- Finally being OK not fixing my 11-year-old car and walking into the dealership to buy a new model without guilt
- Maybe even fly first class to Honolulu, but that seems unnecessary since the flight is relatively short and the kids are small and don’t care
I am working toward most of these goals right now the slow way, one monthly contribution at a time. The lockup creates a parallel universe where all of it could happen at once. That is exhilarating and destabilizing in equal measure.
And yes, I know investing in VCX pre-listing is not the same as working at a startup and earning stock grants. But I could have invested the money anywhere, and I chose to reinvest plenty of what I earned from the Fundrise partnership back into their products.
Since 2023, my thesis has been to invest in AI as a hedge against the tougher labor market my children will likely face. I plan to maintain that thesis until they both graduate from college, then reassess. My skin in the game is real, even if I never had to badge into an office for it.
The Uncertainty Is The Hardest Part
Here’s what separates a lockup from ordinary market volatility: agency. When a regular stock I own tanks, I can sell, buy more, or do nothing. Bad outcomes are possible, but they’re my outcomes. During a lockup, you are strapped to the mast like Odysseus, forced to listen to the social media sirens sing about the ticker for six months while your hands stay tied.
The number on the screen is not money. It is a rumor about money. And for VCX, the rumor has two moving parts: the NAV, which grinds along with funding rounds and IPOs, and the premium, which swings with retail mood. You only get paid on the product of the two, on one specific date you did not choose.
I learned this lesson viscerally. VCX debuted around $19. Within weeks, it temporarily rocketed past $400, a level I never imagined in my wildest dreams. The euphoria was incredible. Then it came back to earth, and now trades around $65-$70. Still a wonderful gain from the debut price, but a fraction of the peak.
Watching those extraordinary paper gains evaporate was numbing. One by one, the dreams I listed above began to vanish. The Honolulu estate went first. Then the paid-off rental mortgage. Then the luxury cruise got downgraded to a nice dinner at McDonald’s. There wasn’t much I could do except watch.
Endless Variables To Consider Before And After Lockup
So the uncertainty compounds in every direction. Anthropic could IPO before the lockup expires, or after. The market could melt up, or crack. The premium could hold, or finish its collapse. I’ve run multiple scenarios in a spreadsheet and through AI, and all the modeling in the world doesn’t change the one variable that matters: I cannot act until the date arrives.
After a career of analyzing risk, I thought I had felt every flavor of market anxiety. I hadn’t. There is something uniquely humbling about watching your net worth fluctuate dramatically while being contractually forbidden from doing anything about it. Hedge is possible, but expensive. And there are no perfect hedges in this situation.
Through it all, I kept reminding myself to stay humble, to keep fixing my 11-year-old junker of a car, and to keep scrubbing my own toilets. The numbers were never real in the first place, except for the unrestricted shares I got to sell. Talk about facing the marshmallow test on maximum difficulty!
The Fear Of Missing Out On More Upside As Well
Then there is the other side of uncertainty. The fear is not just about losing what you have. It is also about selling too soon after lockup and missing what comes next.
Say you started with $100,000 in VCX pre listing. By lockup expiration it has grown to $400,000, reflecting NAV growth and a significant premium. You need the money for something real, so you sell.
Three years later, with the NAV up another 200%, that position would have been worth roughly $1.2 million. You gave up a life changing outcome for a merely great one. Great outcomes are great! But greed can make you dissatisfied.
This is why the Dumbbell FIRE Investing Method is so powerful. Once your investments cover all your living expenses, you can afford to invest aggressively with the rest of your capital.
You never go broke taking profits. There have certainly been plenty of IPOs that have floundered since listing. Then again, plenty of companies do well post IPO as well.
The Discipline Not To Spend Money You Don’t Have Yet
The most dangerous phase of a windfall is before it arrives. Mentally spending paper gains is free entertainment. Actually spending them is how people blow up.
Startup employees sometimes fall into this trap. They buy the Porsche at the IPO pop, sign the mansion mortgage against unvested shares, then watch the stock drop 80% before their window opens. The gain was never theirs. The debt very much is.
So here are the four rules I’m following until the money actually settles:
- Apply a 50% haircut or assume initial price only. For any planning purpose, I value my locked shares at half the current market price, or the strike price I was granted at purchase, whichever is lower. If the real number ends up higher, wonderful. If not, nothing in my life breaks.
- Take on zero new obligations. No new debt, no contracts, no verbal commitments backed by paper gains. Better yet, simply life by reducing obligations. We got rid of cable and don’t miss it one bit.
- Keep lifestyle at pre-listing levels. Same grocery store, same house cleaning routine, same 11-year-old car with charming electrical gremlins. Lifestyle inflation should lag windfalls by at six months, not lead them.
- Remember your silent partner. The IRS is locked up right alongside me, and unlike me, their shares always vest. Any proceeds are a pre-tax fantasy until I model the actual bite, which can easily be 32% – 42%.
Patience is easy to preach and hard to practice when a life-changing number stares at you every morning. But six months of discipline is a cheap price for not having to explain to your partner why you owe money on a house you bought with shares you didn’t have.
Unexpected Emotions From The Lockup
Beyond the fear and the greed, a lockup surfaces additional feelings I did not expect.
The secrecy. You can’t really talk about it in real life. Mention a potential windfall to friends and you’re bragging. Complain about lockup anxiety and you’re insufferable. So you stay quiet, which gets lonely, because the biggest financial event of your year is happening in a soundproof room. This is stealth wealth in its purest form: practiced not by choice, but by social necessity.
The superstition. Part of the reason I sat on this post for four months is that some ancient part of my brain believes writing about VCX will jinx it. I have an MBA and 30 years of investing experience, and I’m still wary about disturbing the animal spirts. I feel much better publishing this post after the mania exited, and months after my initial podcast recording on March 25, 2026: Why VCX Has Soared And What Investors Should Do Now (Apple, Spotify).
The greed creep. When VCX listed, I would have been thrilled with a 50% gain. But it went on to 20X at one point, so the bar for what I’d be happy with increased. My goal now is to recalibrate back to modest expectations.
The time distortion. Six months is nothing. I’ve held real estate and stocks for well over a decade. But a lockup turns you into a kid counting days until summer vacation. If you think about it, the days begin to crawl. The lockup expiration date manages to feel both imminent and impossibly far away.
The gratitude, eventually. Sit with all of the above long enough and something softens. You eventually begin to simply appreciate being in the position to potentially do well financially. If you don’t, that’s OK too.
What Is VCX Actually Worth?
The short version: VCX’s NAV was $18.97 at listing. Since then, Anthropic, its largest holding, marked up roughly 5X after raising at a $965 billion post-money valuation. OpenAI, SpaceX, Anduril, and others have all raised or listed at significantly higher valuations too.
My math points to a NAV of roughly $40/share by the time my lockup expires around September 19, 2026, more than double the listing NAV in six months.
The full three-step framework, the charts, and my base and bull case scenarios through 2028 deserve their own post. So stay tuned for a detailed analysis of VCX’s NAV next. Because just like buying stocks, you’re buying for future potential earnings growth.
If you own VCX, or you’re thinking about buying it, please read that post before doing anything. The gap between the NAV and the share price is where fortunes get made and lost.
Dream The Best Case, Not Just The Worst
Most of us default to imagining disasters before we act. It keeps us safe. But it also limits our potential.
In October 2011, hiking in Santorini, I first let myself imagine leaving finance for good. The dream felt absurd at 33. So I ran the numbers and devised a plan. Severance, passive income, worst case, best case.
The math said the dream was irresponsible. I took the leap in April 2012 anyway. More than 14 years later, I’m still here. Still writing. Still surprised by what’s possible when you model the upside with the same rigor you model the downside.
Whatever the VCX shares are worth when the lockup expires, I’m grateful for all of it. Even the anxiety.
Especially the anxiety. It means something real is at stake.
Questions: To startup employees who joined pre-IPO and experienced a successful listing: how did you manage the six-month lockup? What do you wish you had known going in? Did you feel the pull to pre-spend your paper gains? And how do you decide how much of a winner to sell when you finally can?
The Next VCX
Fundrise has reportedly filed to launch VCX 2, though timing and final structure remain uncertain. What I know for sure: I’d rather invest at NAV than at potentially a multiple of NAV post listing. If a sequel launches, existing Fundrise investors will be notified first.
In the meantime, Fundrise offers private real estate and credit funds worth exploring. With rates still elevated, private credit continues to generate attractive yields. And with so little housing built since 2022, I expect upward pressure on rents and home prices for years. Compared to stocks near record highs, commercial real estate remains inexpensive.
I’ve personally invested over $650,000 with Fundrise, a long-time sponsor of Financial Samurai.