Nobody tells you the truth about startups at the beginning.
You hear about the garage, the late nights, the big launch, the funding round, the founder on a magazine cover. You don’t hear about the board meeting where the founder gets fired. You don’t hear about the money that went somewhere it shouldn’t have. You don’t hear about the lawyers.
I heard about all of it — from one person. His name is William Christopher Skelley. He was my first real business teacher.
This is my thank-you to him. It is also an honest one. If you search his name, you will find a U.S. Securities and Exchange Commission case. I won’t pretend it isn’t there. In a strange way, it is part of what he taught me.
Who is William Skelley?
William is an American entrepreneur and real estate investor. Early in his career he worked with startups in Silicon Valley and Boston on fundraising, marketing, operations and boards. He also worked at General Electric, Bain Capital and Olympus, and later at Rose Park Advisors, the Boston investment firm co-founded by Harvard professor Clayton Christensen — the man who gave the world the idea of “disruptive innovation.” He studied in Harvard Business School’s Owner/President Management program.
In 2012 he co-founded iFunding, one of the first real estate crowdfunding platforms in the United States. The idea was simple and, at the time, new: let ordinary investors put money into real estate projects online, in small amounts, instead of leaving those deals to banks and the very rich. It got attention from CNBC, The Wall Street Journal, The Real Deal and others.
Today he lives between Da Nang, Vietnam and Bali, invests in short-term rentals in Southeast Asia, and advises young companies on raising capital and growing. One of those companies is mine: William chairs the board of advisers at Santara AI, which I co-founded. I want that to be clear before you read any further.
How we met
We didn’t meet at a conference or over a long dinner. We met on a WhatsApp call.
There was no small talk. About five seconds after we said hello, we were already talking business — about HiTaVa, the spreadsheet-template business for small companies that I co-founded with my girlfriend. (To be fair to her: she runs almost everything there.) Who are the customers, what do they pay, what do we build next? Most people would find that too fast. For me, it was perfect. I knew right away I had found someone who works the way I do.
We are both workaholics. We think about the next problem while we are still solving the current one, and we would rather spend an hour on a hard question than ten minutes on polite conversation. That first call set the tone for everything that came after.
What he taught me
I came to William knowing how to write code. I didn’t know how business worked. He didn’t teach me with slides. He taught me with stories — real companies, real founders, real money — and he never cleaned them up.
Lesson 1: Every startup lives in two worlds
There is a light world. It is the one in the pitch deck: a bold idea, a small team that won’t quit, a product that makes people’s lives better. This world is real. It is the reason people start companies at all.
And there is a dark world. It is the one nobody puts in the deck:
- the pressure to show growth every single month, at any cost;
- the story that gets bigger than the numbers behind it;
- the founder who starts believing their own hype;
- the “small” shortcut that nobody will notice — until someone does.
Most startup advice only shows you the light world. William showed me both, on purpose. His point was that you can’t protect yourself from the dark world if you don’t know it exists.
Lesson 2: The founder works for the investors
This one surprised me most.
I used to think the founder was the boss. You have the idea, you build the company, you’re in charge. Right?
William said: not after you take outside money.
Once investors put money into your company, they get shares, and often seats on the board. The board can hire the CEO, and the board can fire the CEO. The CEO, the CFO, even the founder who started everything — in the end, they all work for the people who funded the company.
He made the point with two stories that every founder should know.
Adam Neumann and WeWork
Adam Neumann turned WeWork from a single shared office in New York into one of the most valuable startups in the world, with Japan’s SoftBank as its biggest backer. He was charismatic, ambitious, and very good at telling a story.
Then, in 2019, WeWork tried to go public. To sell shares on the stock market, a company has to open its books, and when people looked closely, they did not like what they saw. Neumann had leased buildings he partly owned back to WeWork. The company had paid him millions of dollars for the rights to the name “We” (he later gave the money back). His control over the company was almost total.
The public offering collapsed. Within weeks, the investors pushed Neumann out as CEO of the company he had created.
Travis Kalanick and Uber
Travis Kalanick built Uber into a global giant by being aggressive about everything — cities, competitors, regulators. For years, investors loved it, because it worked.
Then came 2017: a string of scandals about Uber’s workplace culture and the way it did business. In June of that year, a group of Uber’s major investors, led by the venture firm Benchmark, demanded that Kalanick resign. He did. Benchmark later even sued him in a fight over control of seats on the board.
The founder who built Uber was removed by the people who paid for it.
What the two stories have in common
William was careful about the lesson. It wasn’t “investors are the enemy.” It was this:
When you take someone’s money, you take on a duty to them.
Founders who forget that duty — who treat the company like it belongs only to them, or who blur the line between the company’s money and their own — eventually lose the company. Sometimes they lose much more.
Lesson 3: Learn the game before you play it
William believed passion gets a company started, but understanding keeps you alive. Before you raise a single dollar, he said, you should understand:
- the cap table — who owns what percentage of the company;
- the term sheet — the deal you are actually signing, not the one you hope you’re signing;
- the board — who sits on it, how they vote, and who can replace you;
- your duty — to the people whose money you are holding.
This is not the exciting part of startups. It is the part that decides who is still standing five years later.
The part of the story I can’t skip
Here is the part that is hard to write.
In September 2018, the SEC filed a civil fraud lawsuit against William and his iFunding co-founder, Sohin Shah, in federal court in New York. The SEC alleged that:
- they raised more than $3 million from 42 investors in 17 states to build the iFunding platform;
- more than $1 million of that money was used for personal expenses;
- the offering documents investors received contained false statements about how the money would be used, how many real estate projects iFunding had financed, and how much money the platform had raised.
William did not respond to the lawsuit. In July 2019 the court entered a default judgment against him and permanently barred him from violating the anti-fraud rules of U.S. securities law. In March 2021 the court ordered him to pay about $1.07 million in disgorgement (giving back the money), about $185,000 in interest, and a $1.07 million civil penalty — roughly $2.33 million in total. His co-founder settled separately without admitting or denying the claims. As far as I can find, this was a civil case only; I found no record of criminal charges.
What William says about it
William has written about this himself, in a post on his own blog called What I Signed, What It Cost, and What I’d Tell Any Founder Now.
In his telling, the offering documents did not disclose company expenses such as travel, entertainment, an apartment and office costs, and he signed them without reading them closely enough. He doesn’t hide behind whoever drafted them. He says that as the CEO who signed, he owned every word. He also writes that money invested in the real estate deals themselves was properly accounted for — but adds that this is not the point.
His lesson for founders fits in one line:
“If you sign it, you own it — every word.” — William Skelley
You can decide for yourself how much weight to give his account. I am telling you both sides because you deserve both.
What I think
I am not writing this to defend what happened. Forty-two people trusted iFunding with their money. They deserved the full truth about where it went. That matters more than anything William taught me.
But here is the irony I keep coming back to. The man who taught me that founders work for their investors ended up in court because, according to the SEC, investors were not told the truth about their money. William didn’t just tell me about the dark world of startups. His own story became the clearest example of it.
And yet, he doesn’t hide from it. He writes about it openly now, as a warning to other founders. I think that is worth something. A person is more than their worst chapter, and the lessons he gave me were real.
Nobody is perfect
William isn’t perfect. Neither am I. Neither is anyone reading this.
What I respect is what he did next. He didn’t walk away from business, and he didn’t pretend the past never happened. He owned the mistake, learned from it, and changed how he works. Today he is the first to tell a young founder to read every word before signing, and to treat investors’ money as a duty, not a prize.
He has also built a life beyond work. He has his own family now, with two children, and when you meet him today, you meet someone who knows exactly what is at stake when you get things wrong — and why it matters to get them right.
And through all of it, one thing about him never changed: William is a superstar at building things from zero. Give him an empty room, a rough idea and a few people, and he will turn it into a plan, a pitch and a company. He did it in New York with iFunding, back when almost nobody believed real estate could be sold online. He is doing it again now in Southeast Asia. That talent is the reason I learned so much from him in the first place.
The lessons I carry
If I could put everything he taught me on one card, it would say:
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Startups have a light side and a dark side. Know both.
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Once you take investors’ money, you work for them. Never forget it.
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Learn the game — cap table, term sheet, board — before you play.
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Read every word you sign. If you sign it, you own it.
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Ambition without transparency eventually costs you everything you built.
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Nobody is perfect. Own your mistakes, learn, and build again.
The first three he taught me with words. The last three he taught me with his own life.
Every time I talk to an investor, report to a client, or sign anything at Santara, I think about them.
Thank you, William
Thank you for being my first business teacher — for showing me the light world and the dark world, and for being honest about which one you ended up in. Thank you for showing me that a mistake doesn’t have to be the end of the story, and that you can always build again from zero.
I took the lessons. I took the warning too. And I took the courage to start.
Sources: SEC Litigation Releases No. 24288 (Sept. 26, 2018), No. 24536 (July 2019), and No. 25066 (Mar. 26, 2021), SEC v. Skelley and Shah, No. 18-cv-8803 (S.D.N.Y.); William Skelley, williamskelley.com and his post “What I Signed, What It Cost, and What I’d Tell Any Founder Now” (Aug. 2026). Background on WeWork and Uber is from widely reported news coverage of 2017–2019.
Follow-up: Read Every Word You Sign: Term Sheets for First-Time Founders, a plain-language guide to the document where founders and investors decide who controls the company.
