In 2012, I started a company alone in a one-bedroom apartment in New York City, funding it with my own money. Within a few years, iFunding was one of the best-known names in real estate crowdfunding; I was appearing on CNBC, and we had raised more than $30 million from investors. A few years after that, I was a defendant in a lawsuit filed by the Securities and Exchange Commission.
This is the article I've avoided writing for a long time. Not because I'm hiding from what happened — the case is public record, and anyone can read it — but because it took me years to understand the lessons well enough to be useful to anyone else. I'm writing it now because I meet founders every week who are making the exact mistakes I made, at the exact stage I made them, with the exact confidence I had that it would all be fine.
It won't all be fine. Not unless you do the unglamorous work early. Here's my story, and what I'd tell you to do differently.
The rise
When Title II of the JOBS Act took effect, it changed everything for private capital raising. For the first time, companies could publicly market securities offerings to accredited investors. Real estate was the obvious first frontier, and iFunding was one of the earliest platforms in the space.
I was the sales team — the entire sales team. Every dollar we raised, I raised. I worked around the clock, traveled constantly, and entertained investors across the world for five years. I paid myself less than an entry-level analyst on Wall Street and put everything back into the company. There was a stretch early on when I was getting eviction notices on my door because every dollar I had went into the business. Then, seemingly overnight, I was on national television talking about the future of real estate investing.
That contrast — eviction notices to CNBC — should have been a warning sign, not a badge of honor. We were scaling our profile far faster than we were scaling our infrastructure. The company had my hustle. What it didn't have was the corporate machinery a business handling other people's money absolutely requires.
What went wrong
The short version: the disclosures in our offering documents did not match reality, and I signed them.
When we raised our $2 million seed round, our legal team and COO prepared the private placement memorandum. I wasn't deeply involved in drafting it — I was out raising the money and running the business. But I signed it, and that signature made me responsible for every word, including the words that weren't there.
It later came out — through an internal investigation I commissioned, using an outside consultant with decades of Wall Street compliance experience — that several expense-related disclosures had not been properly made: things like travel and entertainment, employee phones, office expenses, and a corporate apartment that employees used. When the picture became clear, I made the hardest operational decision of my career: I let go of essentially the entire team and brought in a more senior group. We began restating our financials and informing investors.
We were in the middle of that process when the SEC subpoena arrived.
What it cost
In September 2018, the SEC filed a civil suit against me and my co-founder, alleging misappropriation of investor funds and materially misleading statements to investors. In March 2021, the court entered a final judgment against me: an order not to violate securities laws again and a monetary judgment of more than $2 million, including disgorgement, interest, and a penalty.
I could spend paragraphs on context — that the SEC's initial investigation into project-level funds found the investor money in our real estate deals was accounted for, that our portfolio delivered a net return of 12.3% across all investments at the time I left, that the month we received the subpoena was ironically our first profitable month. All of that is true, and none of it is the point. The point is that I was the CEO. The documents were wrong, I signed them, and the consequences were mine to carry.
The financial judgment was only part of the cost. I lost the company I had spent nearly a decade building. I lost a fortune in legal fees and settlements. I lost the reputation I had constructed, carefully, interview by interview and deal by deal. For a long time, I wasn't sure what, if anything, I would be allowed to build next.
The lessons
If you sign it, you own it — every word. You can hire an internal general counsel. You can pay an outside firm tens of thousands of dollars to draft your offering documents. None of that transfers an ounce of your responsibility. When I signed that PPM without reviewing every line, I wasn't delegating work — I was delegating my own accountability, which is the one thing a founder cannot delegate. Read every word of anything you sign, even if you're the only person on earth who ever does.
Fiduciary duty is not a vibe. It's the job. When you take other people's money, you stop being just an entrepreneur and become a fiduciary. That word felt abstract to me at 30. It doesn't now. Every expense, every disclosure, every representation to an investor is part of a duty that follows you personally — no matter what anyone advised you, no matter who actually made the error.
Build the boring infrastructure before you need it. My biggest structural mistake wasn't any single document. It was scaling a high-profile, heavily regulated business on a startup's administrative skeleton. If your company touches securities, you need experienced compliance and finance people in the room from the start — not after the seed round, not once you've "made it." The compliance hire you think you can't afford is dramatically cheaper than the settlement, and infinitely cheaper than the decade of reputational cost.
Being the hardest worker in the room is not a defense. I worked 24/7/365 and assumed effort equaled diligence. It doesn't. You can outwork everyone and still fail the people who trusted you, because trust isn't earned through hours — it's earned through controls, transparency, and verification. "I was too busy keeping my head down and hustling" is an explanation. It is not an excuse. I know, because I lived the difference.
When you find a problem, run toward it. The decisions I'm least ashamed of are the ones that hurt most at the time: commissioning the internal investigation, replacing the team, restating the financials, telling investors. Cleaning up honestly didn't spare me the lawsuit. But it's the reason I can write this article and look at myself while doing it. If you discover something wrong in your company, disclose it fast and fix it faster. The cover-up instinct is the true company killer.
There is life on the other side — if you actually change. The years after the case were the hardest of my life. I lost the company I built, a fortune in legal costs and judgments, and the version of my reputation I'd spent a decade constructing. What I didn't lose was the ability to start again — smaller, quieter, and structurally different.
Where I am now
Today I live in Southeast Asia. I work with startups across the region, and I'm building again. I serve in governance-conscious roles, with real boards, real counsel, and documents I read down to the footnotes — because now I know exactly what each word costs.
I'm not writing this to relitigate the past or to ask anyone to see me as a victim. I'm not one. I'm writing it because the founder reading this at 1 a.m. — the one raising money on adrenaline, signing documents between flights, certain that the legal details are someone else's job — is me, twelve years ago. If that's you: stop. Read what you sign. Hire the boring people. Treat every investor dollar as the sacred obligation it is.
The market forgives failure. It's far slower to forgive carelessness with other people's money. Learn that from my story, so you never have to learn it from your own.