Earlier than I die, I’ve a complete bucket listing I wish to get by. One merchandise is experiencing what it is prefer to be a startup worker whose firm goes public. For those who’re contemplating becoming a member of a startup, or already at one ready to your lockup to run out, this submit 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 appears like to carry doubtlessly 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 realized some other manner.
I’ve waited 4 months to publish this submit to let the preliminary mania die down and provides myself time to mirror. After investing since 1996 and dealing on IPOs from 1999 to 2012, I’ve realized that performing on investing FOMO is usually detrimental to constructing wealth. Higher to write down with a transparent head than a euphoric one.
The Aim 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 neatest thing. I invested in each public tech firm that stated no. I then put cash into conventional enterprise capital funds for personal firm publicity. If I couldn’t sit at their desk, at the very least 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 acquired a style of startup vitality. 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 inventive 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 pal linked me with a fintech firm on the Collection Seed stage, and I gave it 4 months. Good folks, however not the expansion trajectory and match I used to be on the lookout for. Finally, the corporate was acquihired, so no IPO there both.
I stored looking for the sensation I couldn’t identify.
Had The Greatest Startup Job All Alongside. I Simply Didn’t Acknowledge 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 accomplice and person since 2016. What began as a real seek for actual property diversification into the heartland and away from costly San Francisco property changed into one of the crucial enduring skilled relationships of my post-finance life.
I developed the BURL framework (Purchase Utility, Lease Luxurious), which argues for investing in lower-cost areas of the nation for larger revenue 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 business actual property acquired hit beginning in 2022 because the Fed hiked aggressively, I didn’t stroll away. I stored writing, stored analyzing, stored being trustworthy about each the challenges and the long-term thesis.
That loyalty ran each methods. Fundrise stored investing within the relationship too. At the moment, Fundrise manages over $3 billion in residential and industrial actual property, plus a $1.5+ billion publicly listed enterprise fund anyone should purchase 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 trade for fairness that is likely to be price one thing sometime, you commit your time, your vitality, and years of your profession. You report back to a boss. Sit by 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 way in which, 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 accomplice and investor throughout their merchandise, I profit when Fundrise does effectively, just like an worker with fairness. However my “job” is solely to do what I’d do anyway: analysis, analyze, and write about investments I really personal.
In the meantime, I’ve no conferences, no KPIs, no direct studies, and no enterprise journey. I acquired to spend the final decade elevating my two children and enjoying pickleball at 10 am on Tuesdays. That is a reasonably good gig!
None of this is able to imply a lot with out Fundrise executing on their finish. The VCX itemizing on the NYSE took years of planning and constructing to tug off.
I bear in mind speaking with Ben Miller (Apple podcast), Fundrise’s CEO, throughout COVID about his concept to launch a public enterprise product. Loads of folks advised him it could not be finished. 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 acquired the Airbnb or Uber provide. It seems I acquired one thing arguably higher: startup upside with out giving up the liberty I retired to seek out.
What The 6-Month Lockup Really Feels Like
If in case you have by no means been by 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 Could 1999, and Credit score Suisse was already public after I hopped over.
You’ve got shares. The shares have a value. That value represents a quantity that might change your life in concrete, particular methods. And you can not contact any of it, normally for six months.
Each morning you verify the worth. 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’s actual 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 not assist dreaming about what you would do with the proceeds. I’ve been an enormous dreamer since I used to be a child. Dreaming is free, so why not dream large? You by no means know what may occur, and an optimistic angle tends to pay dividends in life, relationships, investing, profession, and household.
I bear in mind one night in 1999, leaving the workplace at 9pm after arriving at 5:30am, dreaming about retiring by 40. That dream changed into a recreation plan, which changed into a negotiated severance that allow me go away six years forward of schedule. Goals have a humorous manner of changing into blueprints.
Submit-listing, listed here are a number of the issues I’ve caught myself dreaming about:
- Superfund 529 plans for grandchildren I would not have but
- Take my mother and father on a real around-the-world luxurious cruise, the sort they might by no means ebook for themselves
- Write a six-figure verify to the Pomeroy Middle, which serves folks with disabilities
- Write a six-figure verify to my youngsters’s college to assist construct out the grounds and supply extra tuition help 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
- Purchase an property in Kahala, Honolulu, a block from the seaside and stay in the identical metropolis as my mother and father
- 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 top quality to Honolulu, however that appears pointless for the reason that flight is comparatively quick, the youngsters are small, and it units a foul precedent
I’m working towards most of those objectives proper now the gradual manner, 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 shouldn’t be the identical as working at a startup and incomes inventory grants. However I may have invested the cash anyplace, 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 spend money on AI as a hedge towards the harder labor market my youngsters 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 recreation 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 bizarre market volatility: company. When a daily inventory I personal tanks, I can promote, purchase extra, or do nothing. Dangerous outcomes are attainable, however they’re my outcomes. Throughout a lockup, you might be strapped to the mast like Odysseus, pressured to hearken to the social media sirens sing in regards to the ticker for six months whereas your fingers keep tied.
The quantity on the display screen shouldn’t be cash. It is a rumor about cash. And for VCX, the rumor has two transferring components: the NAV, which normally grinds greater with new 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 realized this lesson viscerally. VCX debuted round $19. Inside weeks, it quickly rocketed previous $400, a stage I by no means imagined in my wildest desires. The euphoria was unbelievable. Then it got here again to earth, and now trades within the mid-$60s. Nonetheless a great achieve from the debut value, however a fraction of the height.
Watching these extraordinary paper good points evaporate was numbing. One after the other, the desires I listed above started to fade. The Honolulu property went first. Then the paid-off rental mortgage. Then the luxurious cruise acquired 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 course. Anthropic may IPO earlier than the lockup expires, or after. The market may soften up, or crack. The premium may maintain, or utterly collapse. I’ve run a number of eventualities in a spreadsheet and by AI, and all of the modeling within the world does not change the one variable that issues: I can not act till the date arrives.
After a profession of analyzing threat, I thought I had felt each taste of market anxiousness. I hadn’t. There’s something uniquely humbling about watching your internet price fluctuate dramatically whereas being contractually forbidden from doing something about it. Hedging is feasible, however costly. And there are not any excellent hedges on this state of affairs.
By way of all of it, I stored reminding myself to remain humble, to maintain fixing my 11-year-old junker of a automobile, and to maintain scrubbing my bathrooms. The numbers have been by no means actual within the first place, apart from the unrestricted shares I acquired to promote. Speak about dealing with the marshmallow check on most issue!
The Worry Of Lacking Out On Extra Upside As Properly
Then there may be the opposite aspect of uncertainty. The concern isn’t just about shedding what you will 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 major 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 consequence for a merely nice one. Nice outcomes are nice! However greed can nonetheless make you dissatisfied.
That is why the Dumbbell FIRE Investing Methodology is so highly effective. As soon as your investments cowl all of your residing bills, you may afford to speculate aggressively with the remainder of your capital.
You by no means go broke taking income. There have actually been loads of IPOs which have floundered since itemizing. Then once more, loads of firms do effectively submit IPO as effectively.
The Self-discipline Not To Spend Cash You Do not Have But
Essentially the most harmful part of a windfall is earlier than it arrives. Mentally spending paper good points is free leisure. Really spending them is how folks blow up.
Startup staff typically fall into this entice. They purchase the Porsche on the IPO pop, signal the mansion mortgage towards unvested shares, then watch the inventory drop 80% earlier than their window opens. The achieve 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 actual quantity finally ends up greater, great. If not, nothing in my life breaks.
- Tackle zero new obligations. No new debt, no contracts, no verbal commitments backed by paper good points. Higher but, simplify life by lowering obligations. We removed cable and do not miss it one bit.
- Preserve life-style at pre-listing ranges. Similar grocery retailer, similar home cleansing routine, similar 11-year-old automobile with charming electrical gremlins. Way of life inflation ought to lag windfalls by at six months, not lead them.
- Keep in mind your silent accomplice. The IRS is locked up proper alongside me, and in contrast to me, their shares all the time vest. Any proceeds are a pre-tax fantasy till I mannequin the precise chunk, which may simply be 32% – 42%.
Persistence is simple to evangelise and exhausting to follow when a life-changing quantity stares at you each morning. However six months of self-discipline is an inexpensive value for not having to clarify to your accomplice why you owe cash on a home you got 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 discuss it in actual life. Point out a possible windfall to pals 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 type: practiced not by alternative, however by social necessity.
The superstition. A part of the explanation I sat on this submit for 4 months is that some historical 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 submit 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’d have been thrilled with a 50% achieve. But it surely went on to 20X at one level, so the bar for what I might be pleased with elevated. My purpose now could be to recalibrate again to modest expectations.
The time distortion. Six months is nothing. I’ve held actual property and shares for effectively over a decade. However a lockup turns you into a child counting days till summer season trip. The lockup expiration date manages to really feel each imminent and impossibly distant.
The gratitude, finally. Sit with the entire above lengthy sufficient and one thing softens. You finally start to easily admire being within the place to doubtlessly do effectively financially. For those who do not, that is OK too.
What Is VCX Really 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 greater valuations too.
My math factors to a NAV of roughly $40 per share by the point my lockup expires round September 19, 2026, greater than double the itemizing NAV six months earlier. However what I am actually wanting ahead to is the potential NAV development in 2027 and 2028, to $80 or extra per share, as its holdings proceed to compound.
In fact, personal valuations can reverse shortly, so I am not counting any chickens. AI valuations particularly have run exhausting, and a funding winter would hit a enterprise fund’s NAV with a lag. I will imagine the good points after I can really promote the shares.
The total three-step framework, the charts, and my base and bull case eventualities by 2028 deserve their very own submit. So keep tuned for an in depth evaluation of VCX’s NAV subsequent.
For those who personal VCX, otherwise you’re fascinated by shopping for it, I might learn that submit earlier than doing something. The hole between the NAV and the share value is the place fortunes get made and misplaced.
Dream The Greatest Case, Not Simply The Worst
Most of us default to imagining disasters earlier than we act. It retains us protected. But it surely 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 revenue, worst case, greatest case.
The mathematics stated 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 while 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 identified getting into? Did you’re feeling the pull to pre-spend your paper good points? And the way do you determine how a lot of a winner to promote while you lastly can?
The Potential Subsequent VCX
Fundrise has filed to launch VCX 2, although timing and ultimate construction stay unsure, and there is nothing to purchase as we speak. What I do know for positive: I might moderately make investments at NAV than at a a number of of NAV post-listing. If a sequel launches, present Fundrise traders shall be notified first.
Within the meantime, Fundrise presents personal actual property and credit score funds price exploring. With charges nonetheless elevated, personal credit score continues to generate engaging 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 document highs, business actual property stays cheap.
I’ve personally invested over $650,000 with Fundrise, a long-time sponsor of Monetary Samurai.
