Earlier than I die, I’ve an entire bucket listing I wish to get via. One merchandise is experiencing what it is prefer to be a startup worker whose firm goes public. Should you’re contemplating joining a startup, or already at one ready to your lockup to run out, this publish is for you.
I spent 13 years in banking serving to firms go public. I noticed the champagne, the headlines, the in a single day multi-millionaires. However I by no means actually understood what it felt prefer to be on the within, till now.
That lastly modified on March 19, 2026, when the Fundrise Innovation Fund, VCX, listed on the NYSE. For the primary time, I perceive what it looks like to carry probably life-changing cash that is locked up for six months. The expertise has additionally taught me a brand new dimension of investor psychology I could not have discovered some other approach.
I’ve waited 4 months to publish this publish to let the preliminary itemizing mania die down and provides myself time to mirror. After investing since 1996 and dealing on IPOs from 1999 to 2012, I’ve discovered that appearing on investing FOMO is mostly detrimental to constructing wealth. Higher to jot down with a transparent head than a euphoric one.
The Objective I May By no means Fairly Attain
Once I left finance in 2012, I needed the total startup expertise. I lived in San Francisco, in spite of everything, the startup capital of the world. I utilized to Airbnb at a $3 billion valuation, then to Uber when it was nonetheless scrappy. No luck.
So I did the subsequent smartest thing. I invested in each public tech firm that mentioned no. I then put cash into conventional venture capital funds for personal firm publicity. If I couldn’t sit at their desk, a minimum of their staff can be working to develop my capital.
However the curiosity by no means left. From 2013 to 2015, I consulted half time with Empower (beforehand Private Capital) and bought a style of startup power. The fairness I obtained 3.5Xed after Empower acquired Private Capital years later. Not life-changing cash, and never an IPO, however sufficient to substantiate that I loved startup tradition.
After that I traveled with my spouse following her creative severance negotiation in 2015, then spent six years absolutely immersed in fatherhood beginning in 2017. In late 2023, the itch got here again. A VC buddy linked me with a fintech firm on the Collection Seed stage, and I gave it four months. Good folks, however not the expansion trajectory and match I used to be searching for. Finally, the corporate was acquihired, so no IPO there both.
I saved trying to find the sensation I couldn’t title.
Had The Finest Startup Job All Alongside. I Simply Did Not Know It.
When Fundrise’s VCX listed and I watched the share value transfer in actual time, one thing clicked.
I’ve been working with Fundrise as an affiliate associate and person since 2016. What began as a real seek for actual property diversification into the heartland and away from costly San Francisco property was some of the enduring skilled 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 nation for higher earnings whereas renting in high-cost areas resulting from low cap charges and higher relative worth. Fundrise turned each a topic I wrote about deeply and a sponsor of Monetary Samurai.
For a decade, that relationship produced constant sponsorship income that I reinvested again into this platform to maintain it free and my very own Fundrise positions. I used to be not simply an affiliate. I used to be a believer. When industrial actual property bought hit beginning in 2022 because the Fed hiked aggressively, I didn’t stroll away. I saved writing, saved analyzing, saved being trustworthy about each the challenges and the long-term thesis.
That loyalty ran each methods. Fundrise saved investing within the relationship too. In the present day, Fundrise manages over $3 billion in residential and industrial actual property, plus a $1.5+ billion publicly listed enterprise fund anyone should buy and promote.
Watching the VCX itemizing unfold, studying the protection, seeing the investor response, I felt one thing I by no means felt watching an IPO from a buying and selling desk.
Then it hit me.
Take into consideration what a startup worker really indicators up for. In alternate for fairness that could be price one thing sometime, you commit your time, your power, and years of your profession. You report back to a boss. Sit via morning standups. Grind towards KPIs, handle folks, and journey when the corporate wants you to.
It is demanding work and the potential fairness upside is what makes the sacrifice price it. Someplace alongside the best way, with out realizing it, I ended up with a model of the upside with out having to make the identical commerce.
As Fundrise’s long-time associate and investor throughout their merchandise, I profit when Fundrise does nicely, much like an worker with fairness. However my “job” is solely to do what I might do anyway: analysis, analyze, and write about investments I really personal.
In the meantime, I’ve no conferences, no KPIs, no direct stories, and no enterprise journey. I bought to spend the final decade elevating my two youngsters and enjoying pickleball at 10 am on Tuesdays. That is a fairly good gig!
None of this might imply a lot with out Fundrise executing on their finish. The VCX itemizing on the NYSE took years of planning and constructing to drag off.
I keep in mind speaking with Ben Miller, Fundrise’s CEO, throughout COVID about his thought to launch a public venture product. Loads of folks informed him it could not be achieved. However after watching him democratize entry to actual property investing since 2012, I used to be enthusiastic he may do the identical for enterprise capital.
I by no means bought the Airbnb or Uber supply. It seems I bought one thing arguably higher: startup upside with out giving up the liberty I retired to search out.
What The 6-Month Lockup Truly Feels Like
When you have by no means been via a lockup interval, let me attempt to describe it precisely. That is technically my first one. I joined Goldman Sachs two months after it went public in Might 1999, and Credit score Suisse was already public after I hopped over.
You will have shares. The shares have a value. That value represents a quantity that might change your life in concrete, particular methods. And you can’t contact any of it, normally for six months.
Each morning you examine the value. You do math in your head. You catch your self designing a future that doesn’t exist but. Then you definitely remind your self that none of it is real till the lockup expires, and also you go about your day carrying this unusual monetary suspense within the background of every little thing.
However you can’t assist dreaming about what you possibly can do with the proceeds. I’ve been an enormous dreamer since I used to be a child. Dreaming is free, so why not dream huge? You by no means know what would possibly occur, and an optimistic angle tends to pay dividends in life, relationships, investing, profession, and household.
I keep in mind one night in 1999, leaving the workplace at 9pm after arriving at 5:30am, dreaming about retiring by 40. That dream was a sport plan, which was a negotiated severance that allow me depart six years forward of schedule. Goals have a humorous approach of turning into blueprints.
Publish-listing, listed here are a number of the issues I’ve caught myself dreaming about:
- Superfund 529 plans for grandchildren I wouldn’t have but
- Take my dad and mom on a real around-the-world luxurious cruise, the type they’d by no means e book for themselves
- Write a six-figure examine to the Pomeroy Center, which serves folks with disabilities
- Write a six-figure examine to my kids’s college to assist construct out the grounds and supply extra tuition assist for households
- Repay the remaining mortgage on a rental property I’ve 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 seaside to be nearer to my dad and mom
- Now not feeling any pressure about paying for impartial grade college tuition
- Lastly being OK not fixing my 11-year-old automobile and strolling into the dealership to purchase a brand new mannequin with out guilt
- Perhaps even fly firstclass to Honolulu, however that appears pointless for the reason that flight is comparatively quick and the youngsters are small and do not care
I’m working towards most of those objectives proper now the sluggish approach, one month-to-month contribution at a time. The lockup creates a parallel universe the place all of it may occur directly. That’s exhilarating and destabilizing in equal measure.
And sure, I do know investing in VCX pre-listing isn’t the identical as working at a startup and incomes inventory grants. However I may have invested the cash wherever, and I selected to reinvest loads of what I earned from the Fundrise partnership again into their merchandise.
Since 2023, my thesis has been to invest in AI as a hedge in opposition to the harder labor market my kids will doubtless face. I plan to take care of that thesis till they each graduate from faculty, then reassess. My pores and skin within the sport is actual, even when I by no means needed to badge into an workplace for it.
The Uncertainty Is The Hardest Half
Here is what separates a lockup from extraordinary market volatility: company. When an everyday inventory I personal tanks, I can promote, purchase extra, or do nothing. Unhealthy outcomes are attainable, however they’re my outcomes. Throughout a lockup, you might be strapped to the mast like Odysseus, pressured to take heed to the social media sirens sing in regards to the ticker for six months whereas your fingers keep tied.
The quantity on the display isn’t cash. It is a rumor about cash. And for VCX, the rumor has two shifting components: the NAV, which grinds together with funding rounds and IPOs, and the premium, which swings with retail temper. You solely receives a commission on the product of the 2, on one particular date you didn’t select.
I discovered this lesson viscerally. VCX debuted round $19. Inside weeks, it quickly rocketed previous $400, a degree I never imagined in my wildest dreams. The euphoria was unbelievable. Then it got here again to earth, and now trades round $65-$70. Nonetheless a fantastic acquire from the debut value, however a fraction of the height.
Watching these extraordinary paper positive aspects evaporate was numbing. One after the other, the goals I listed above started to fade. The Honolulu property went first. Then the paid-off rental mortgage. Then the luxurious cruise bought downgraded to a pleasant dinner at McDonald’s. There wasn’t a lot I may do besides watch.
Limitless Variables To Take into account Earlier than And After Lockup
So the uncertainty compounds in each path. Anthropic may IPO earlier than the lockup expires, or after. The market may soften up, or crack. The premium may maintain, or end its collapse. I’ve run a number of situations in a spreadsheet and via AI, and all of the modeling within the world does not change the one variable that issues: I can’t act till the date arrives.
After a profession of analyzing danger, I thought I had felt each taste of market anxiety. I hadn’t. There’s something uniquely humbling about watching your web price fluctuate dramatically whereas being contractually forbidden from doing something about it. Hedge is feasible, however costly. And there aren’t any good hedges on this scenario.
By all of it, I kept reminding myself to stay humble, to maintain fixing my 11-year-old junker of a automobile, and to maintain scrubbing my very own bogs. The numbers have been by no means actual within the first place, aside from the unrestricted shares I bought to promote. Discuss going through the marshmallow check on most problem!
The Concern Of Lacking Out On Extra Upside As Effectively
Then there may be the opposite facet of uncertainty. The concern is not only about shedding what you could have. Additionally it is about promoting too quickly after lockup and lacking what comes subsequent.
Say you began with $100,000 in VCX pre itemizing. By lockup expiration it has grown to $400,000, reflecting NAV development and a big premium. You want the cash for one thing actual, so that you promote.
Three years later, with the NAV up one other 200%, that place would have been price roughly $1.2 million. You gave up a life altering end result for a merely nice one. Nice outcomes are nice! However greed could make you dissatisfied.
For this reason the Dumbbell FIRE Investing Method is so highly effective. As soon as your investments cowl all of your residing bills, you possibly can afford to speculate aggressively with the remainder of your capital.
You by no means go broke taking earnings. There have actually been plenty of IPOs that have floundered since itemizing. Then once more, loads of firms do nicely publish IPO as nicely.
The Self-discipline Not To Spend Cash You Do not Have But
Probably the most harmful section of a windfall is earlier than it arrives. Mentally spending paper positive aspects is free leisure. Truly spending them is how folks blow up.
Startup employees typically fall into this entice. They purchase the Porsche on the IPO pop, signal the mansion mortgage in opposition to unvested shares, then watch the inventory drop 80% earlier than their window opens. The acquire was by no means theirs. The debt very a lot is.
So listed here are the 4 guidelines I am following till the cash really settles:
- Apply a 50% haircut or assume preliminary value solely. For any planning goal, I worth my locked shares at half the present market value, or the strike value I used to be granted at buy, whichever is decrease. If the true quantity finally ends up increased, fantastic. If not, nothing in my life breaks.
- Tackle zero new obligations. No new debt, no contracts, no verbal commitments backed by paper positive aspects. Higher but, merely life by decreasing obligations. We got rid of cable and do not miss it one bit.
- Hold life-style at pre-listing ranges. Similar grocery retailer, similar home cleansing routine, similar 11-year-old automobile with charming electrical gremlins. Life-style inflation ought to lag windfalls by at six months, not lead them.
- Keep in mind your silent associate. The IRS is locked up proper alongside me, and in contrast to me, their shares at all times vest. Any proceeds are a pre-tax fantasy till I mannequin the precise chew, which might simply be 32% – 42%.
Endurance is straightforward to evangelise and arduous to apply when a life-changing quantity stares at you each morning. However six months of self-discipline is an inexpensive value for not having to elucidate to your associate why you owe cash on a home you purchased with shares you did not have.
Surprising Feelings From The Lockup
Past the concern and the greed, a lockup surfaces further emotions I didn’t anticipate.
The secrecy. You’ll be able to’t actually speak about it in actual life. Point out a possible windfall to buddies and also you’re bragging. Complain about lockup anxiousness and also you’re unbearable. So that you keep quiet, which will get lonely, as a result of the most important monetary occasion of your yr is occurring in a soundproof room. That is stealth wealth in its purest kind: practiced not by alternative, however by social necessity.
The superstition. A part of the rationale I sat on this publish for 4 months is that some historic a part of my mind believes writing about VCX will jinx it. I’ve an MBA and 30 years of investing expertise, and I am nonetheless cautious about disturbing the animal spirts. I really feel significantly better publishing this publish after the mania exited, and months after my preliminary podcast recording on March 25, 2026: Why VCX Has Soared And What Buyers Ought to Do Now (Apple, Spotify).
The greed creep. When VCX listed, I might have been thrilled with a 50% acquire. Nevertheless it went on to 20X at one level, so the bar for what I would be pleased with elevated. My objective now’s to recalibrate again to modest expectations.
The time distortion. Six months is nothing. I’ve held actual property and shares for nicely over a decade. However a lockup turns you into a child counting days till summer time trip. If you consider it, the times start to crawl. The lockup expiration date manages to really feel each imminent and impossibly distant.
The gratitude, finally. Sit with all the above lengthy sufficient and one thing softens. You ultimately start to easily respect being within the place to probably do nicely financially. Should you do not, that is OK too.
What Is VCX Truly Value?
The quick model: VCX’s NAV was $18.97 at itemizing. Since then, Anthropic, its largest holding, marked up roughly 5X after elevating at a $965 billion post-money valuation. OpenAI, SpaceX, Anduril, and others have all raised or listed at considerably increased valuations too.
My math factors to a NAV of roughly $40/share by the point my lockup expires round September 19, 2026, greater than double the itemizing NAV in six months.
The complete three-step framework, the charts, and my base and bull case situations via 2028 deserve their very own publish. So keep tuned for an in depth evaluation of VCX’s NAV subsequent. As a result of identical to shopping for shares, you are shopping for for future potential earnings development.
Should you personal VCX, otherwise you’re fascinated by shopping for it, please learn that publish earlier than doing something. The hole between the NAV and the share value is the place fortunes get made and misplaced.
Dream The Finest Case, Not Simply The Worst
Most of us default to imagining disasters earlier than we act. It retains us secure. Nevertheless it additionally limits our potential.
In October 2011, mountaineering in Santorini, I first let myself think about leaving finance for good. The dream felt absurd at 33. So I ran the numbers and devised a plan. Severance, passive earnings, worst case, finest case.
The maths mentioned the dream was irresponsible. I took the leap in April 2012 anyway. Greater than 14 years later, I am nonetheless right here. Nonetheless writing. Nonetheless stunned by what’s attainable whenever you mannequin the upside with the identical rigor you mannequin the draw back.
Regardless of the VCX shares are price when the lockup expires, I am grateful for all of it. Even the anxiousness.
Particularly the anxiousness. It means one thing actual is at stake.
Questions: To startup staff who joined pre-IPO and skilled a profitable itemizing: how did you handle the six-month lockup? What do you would like you had recognized getting into? Did you’re feeling the pull to pre-spend your paper positive aspects? And the way do you determine how a lot of a winner to promote whenever you lastly can?
The Subsequent VCX
Fundrise has reportedly filed to launch VCX 2, although timing and remaining construction stay unsure. What I do know for certain: I would quite make investments at NAV than at probably a a number of of NAV publish itemizing. If a sequel launches, present Fundrise buyers shall be notified first.
Within the meantime, Fundrise affords personal actual property and credit score funds price exploring. With charges nonetheless elevated, personal credit score continues to generate enticing yields. And with so little housing constructed since 2022, I anticipate upward stress on rents and residential costs for years. In comparison with shares close to report highs, industrial actual property stays cheap.
I’ve personally invested over $650,000 with Fundrise, a long-time sponsor of Monetary Samurai.
