I recently had the pleasure of sitting down with Ed Michelson for our “Inside Startups” LinkedIn Live series. Ed’s one of those people who immediately earns your respect—not just because of his impressive CV, but because of the honesty with which he reflects on it. Former investment banker, ex-founder, now the go-to person for SaaS founders looking to raise money or exit gracefully—Ed’s journey is a study in career reinvention. In this conversation, we went deep into that journey. The scars, the pivots, the failures—and what all of it taught him.
The Polished Start: Investment Banking and the Illusion of Clarity
Like many high achievers in their early twenties, Ed began his career in investment banking—driven by ambition, curiosity, and yes, the appeal of the pay cheque. He described it with a kind of detached amusement, a younger self brimming with energy and invincibility, powering through the long hours and intense workload at Deutsche Bank in New York.
From there, he made the classic move into private equity and eventually into hedge funds. Each move felt like a rung on the ladder. “I kind of pedestalised the private equity space,” he admitted, only to find once inside that it wasn’t what he had imagined. The work was intellectually demanding, yes—but the spark was missing. The passion wasn’t there.
But it wasn’t a moment of crisis. It was more like a slow unravelling of the idea that finance was his forever home.
Asia Calls
While Ed’s financial career was progressing, there was something else quietly pulling at him: Asia. He had studied abroad in Shanghai and caught what he calls “the Asia bug.” After years of telling himself he’d make the move someday, he finally pulled the trigger in 2018. No grand relocation package or cushy expat gig. Just a one-way ticket to Hong Kong and a friend’s couch to crash on.
It took him ten months to find the right role, eventually landing at a hedge fund. It was the logical move—finance was what he knew, and Hong Kong was a global financial centre. But that old restlessness returned. The thrill of the spreadsheets and the deal-making just wasn’t cutting it anymore.
So, like many of us, he dipped his toes into the side-hustle life.
Party Costumes and Humble Pies
His first real swing was classic bootstrapped hustle: a dropshipping business called PartyFunHouse, selling Halloween costumes online in Hong Kong. It was scrappy, underwhelming, and ultimately unsustainable—but it was also, as Ed described it, “a fun learning experience.” That experience—filling orders by hand, trying to market on a shoestring—was humbling, especially for someone who’d come from big-deal finance. The transition from closing multimillion-dollar transactions to tracking down Squid Game costume buyers was as jarring as it was instructive.
That early entrepreneurial sting taught him a critical lesson: pedigree doesn’t convert into traction. “I thought I had the credentials to go off and make a lot of money on my own,” he said, “but I learned quickly how little that mattered when it came to capturing attention, generating interest, and converting.”
That humility would become a running theme.
Chow Time and the Reality of Startup Economics
Eventually, Ed launched a more serious venture—Chow Time, a mobile ordering and payment platform for restaurants in Hong Kong. Think QR code menus, digital receipts, and less pressure on restaurant staff.
On paper, it made sense. COVID had accelerated adoption of touchless payments. Hong Kong had serious staffing challenges in the hospitality industry. The regulatory environment was favourable. All signs pointed to opportunity.
But things didn’t play out that way.
Hong Kong restaurants operate on razor-thin margins. While Ed’s platform added efficiency, it also added cost—especially in the form of online payment processing fees, which ran much higher than the offline status quo. “Restaurants weren’t willing to pay a markup that allowed us to be profitable,” he said. “We ended up giving the solution away for free.”
The business had volume, but not margin. And that, he explained, is a cardinal mistake.
“We had this thesis: if we get enough volume, the margin will come. But the truth is, if you’re not profitable at the unit level from day one, your chances of survival drop significantly.”
Worse still, they outsourced development—no technical co-founder, just burn rate. “I would never do that again,” Ed said. “If your business is built on technology, not having someone internal who can code is setting yourself up for a much harder road.”
What Ed Does Now—and Why It Works
These days, Ed helps SaaS founders at the earliest stages prepare for fundraising. He’s found a sweet spot where his financial pedigree, startup scars, and communication skills converge. His service started organically—he offered free video “roasts” of pitch decks as a lead magnet. They worked. Really well.
So well, in fact, that he launched a full site—RoastMySaaSPitchDeck.com—where founders pay for a brutally honest, insightful critique of their investor materials. It’s a service, yes. But it’s also coaching. And it’s clearly born of someone who knows both sides of the table.
He’s reviewed hundreds of decks. The patterns are familiar: weak problem framing, abstract moats, and founders building solutions to problems they’ve experienced personally without validating them in the market.
His advice? “Don’t just say something is a problem—contextualize it. Quantify it. Show the impact. If customers aren’t actively trying to solve it or willing to pay for it, it’s probably not worth your time.”
Learning in Both Directions
Ed’s humility remains front and centre. While he offers sharp insights and deep experience, he acknowledges that he’s learning from every founder he works with. Each deck, each conversation sharpens his thinking. He knows this isn’t his forever business—but it’s the one that keeps him in the game, acquiring skills, preserving optionality, and waiting for the right opportunity to swing big again.
And when that moment comes, he’ll be ready.
In a world full of posturing and bravado, Ed’s story is refreshingly grounded. He’s open about the mistakes. Clear about the takeaways. And quietly building his next move with intention.
Thanks again for joining, Ed. Let’s do this again sometime.
If you’re a founder, investor, or early-stage team trying to grow something real—without the fluff—I can help. I’m Ben Sheppard: startup coach, C-suite exec, and founder of Silta Finance, a deep-tech company backed by the Asian Development Bank. I’ve helped teams raise millions, close enterprise deals across Europe and Asia, and bring AI products to market in some of the world’s toughest sectors—from infrastructure to M&A.
I don’t do hype. I do clarity, strategy, and execution.
Learn more at bensheppard.xyz
—Ben Sheppard
