While covering the Midwest as a salesman for a private credit firm, Jasdeep Khera had an unusual meeting in Omaha.
Before he could even speak, the advisor he was pitching asked him how much commission he would earn on the deal.
Jasdeep realized his advisor was less interested in ensuring the quality of his investments than in guaranteeing a good commission.
The interaction also encapsulated two fundamental problems he kept seeing repeated over and over in the securities market: The market was filled with too many middlemen and there was too little public information on costs for investors.
Jasdeep realized the alternative investment market was primed for a trimming of middlemen. He founded Yieldwink, a digital platform putting users directly in contact with real estate investments and other alternative securities directly, with no middle-man fees.
In just three years, Jasdeep turned a gap in the alternative securities market into a $275,000 ARR online business. But he had to take a few substantial risks to do it.
Early on, Jasdeep struggled to acquire properties for his platform in a high-competition real estate market. He lived off his savings for a year to source the best deals. And instead of relying on VC money to expand, he capitalized on years of sales experience by strategically tapping into his networks (like hiring the creative director of an ad he liked on TV)
Read on to find out how Jasdeep used his experience from the finance world to create some of the most interesting advisor equity deals we’ve ever heard about at Bootstrappers. Also why he thinks outsourcing work early is in the best interest of every new founder.
The Open Secret of Alternative Investments
Ever since he can remember, Jasdeep had a knack for finance. When he was sixteen, he started investing on howthemarketworks.com, where users invest fake money in real-time stocks. He signed up for monthly trading contests and slowly picked up basic investment strategy.
“I would lose the contests every single month,” Jasdeep says, “but I would watch what the winners did, and I just learned in the process. I had an ETrade account before I had a driver’s license.”
Once he graduated college, Jasdeep put his affinity for finance to work at a traditional New York finance firm. However, his focus shifted away from stocks and bonds when his friend and former coworker, who had been working in alternative investments, convinced Jasdeep to join his firm.
“My buddy’s a great salesman, he took me out for drinks and basically convinced me to jump on board at his his firm,” Jasdeep says. “And once I started learning more about these solutions, I just felt like they were the best-kept secret.”
The alternative investment market includes anything that isn’t stocks, bonds, and cash. Even though alternative securities—like real estate—are often considered the most secure investments, Jasdeep noticed most investors weren’t taking advantage of them.
“In my mind, alternatives are actually the traditional investments—I mean, before you had stocks and bonds, people were buying real estate. It’s like calling Beethoven an alternative musician.”
Jasdeep joined the company as a financial wholesaler—similar to a salesman—covering the Midwest. His main role was meeting with financial advisors to pitch his company’s investments (mostly properties). He also spent hours reading over the fund documents of his competitors.
During four years of research and meetings with financial advisors, Jasdeep gained a deep comprehensive knowledge of the alternative investment market and became convinced of its enormous potential for digitization.
Besides saving gas mileage on his long trips through the Midwest, digitizing alternative investments could eliminate the fee structures that were rampant on his competitors’ fund documents. A digital platform would also allow customers to invest directly instead of through financial advisors, cutting through the middlemen and getting straight to the source.
Jasdeep’s meeting in Omaha convinced him to leap, and in 2022 he launched Yieldwink.
Trading Revenue Now for Returns Later
Jasdeep’s proposition for Yieldwink was that users would invest in properties that the platform itself owned and managed. But, as Jasdeep quickly learned, finding investment properties through a real estate broker puts you in competition with dozens of other buyers, often for a mediocre deal.
To circumvent this, Jasdeep went directly to property owners through cold calling and emailing campaigns. He stuck to multi-family homes, his specialty (Jasdeep has built himself a small personal portfolio over time). With a little luck, he locked down a 40-unit property in Minnesota to begin offering his clients.
During his first year of business, Yieldwink generated very little revenue. Jobless, Jasdeep relied heavily on rental income from his own properties, which meant he was essentially living paycheck-to-paycheck.
“Could we have been profitable in our first year? Yes,” Jasdeep says. “But I wanted to reinvest a lot back into the business—mostly one-time costs, like building out the platform, the website, et cetera.”
Reducing The Risks of Bootstrapping with a Capital Partner
Jasdeep had one personal condition when launching Yieldwink: he couldn’t put investors in a position where they had to take on deals just to generate fees for his revenue.
However, this meant that he was eating into his own paycheck when sourcing deals and was taking on huge personal risk if these deals fell through.
“I knew that if I launched my first deal and wasn’t able to fill that deal, I’d lose all my momentum,” Jasdeep says.
What Jasdeep needed was a way to get extra financial liquidity in a pinch. This is where being a finance guy helped Jasdeep come up with a creative solution to his problem.
“What’s interesting about an operating agreement like an LLC is you can literally do whatever you want,” says Jasedeep.
Jasdeep’s solution was to offer equity in Yieldwink to a highly liquid partner who could step in for him and foot the bill if he lacked the capital to close a deal. This partner could effectively act as a backstop and would receive equity proportional to his cash contributions.
“I found a gentleman who’s been a fantastic operating partner,” says Jasdeep. “He’s built hotels here in New York City and done quick-service restaurants here too. The guy’s multi-talented.”
Luckily, Jasdeep hasn’t had to resort to that cash-for-equity exchange, but finding a trustworthy capital partner earned the trust of early investors on Yieldwink and minimized the risk of his decision to bootstrap.
Feel Stuck? You Might Want to Hire a Consultant
Jasdeep thinks one of his best early investments was hiring consultants—some of whom have remained his advisors to this day.
“The best consultants go out of their way to help you develop new relationships and allow you to tap into their connections,” he says. “Those are the types of people you want, especially for the long-term, for your business.”
The best advisor Jasdeep hired was also the one he hustled the hardest to find. While strategizing about branding for Yieldwink, he recalled a Delta Airlines advertisement he’d seen years ago that had blown him away.
“When I first saw this commercial, I had goosebumps,” Jasdeep says. “When I started my business eight years later, I searched for it on YouTube and I found everyone associated with it.”
He tracked down the writer of the ad and reached out to him on LinkedIn. His timing was just right.
“The guy replied, ‘I’m on paternity leave and I’m happy to help you work on this,’” Jasdeep says. “We started him off on an hourly basis and got a discounted rate in exchange for equity. He built the best branding strategy for us. We’ve been working together for two and a half years now.”
In this way, Jasdeep built Yieldwink’s success on his accumulated knowledge of a niche market, and his willingness to sacrifice cash flow early on ensured future stability for the company.
It Pays to Get Help
Jasdeep recommends that other founders focus all of their energy on the core things that they bring to their businesses. Everything else should be outsourced as soon as possible.
“There are two main components to my business: sourcing good deals and raising capital. If I’m not spending eighty percent of my time on those two things, I’m doing something wrong,” Jasdeep says.
Early on, Jasdeep tried to manage every aspect of the business on his own, sometimes working 100-hour weeks. Not only did it wear him down, it was also extremely inefficient.
“I was learning about funnel marketing, I was learning about how to build the backend myself,” Jasdeep says. “It was just silly stuff that shouldn’t have taken up my time.”
He also says founders should plan for things to move five to ten times slower than they initially thought. In his early projections, he admits, he thought he might be doing five million in revenue today rather than its current six-figures.
But perhaps Jasdeep’s most important trait as a founder is his faith in himself, the company he built, and the value he brings to clients.
“Did I ever have the thought that we would fail? Frankly, I did not,” he says. “And I don’t think we will. I feel pretty confident that we’re going to be alright.”
