I recently spent an afternoon with an old mentor & friend of mine. It’d been seven or so years since our last sit-down conversation. His name is Rishi Shah.
As we shared lunch in my kitchen, it was clear that aspects of our lives had evolved similarly: we’re both dads now, both working on writing books, and both of us remain drawn to the early trenches of entrepreneurship. While other aspects had evolved differently. In prior weeks, I’d been named coach of a 3-year-old T-ball team. In prior weeks, he’d been sentenced to multiple years in prison.
Back in the day, there was a period a time when Rishi and I were quite close. We used to get breakfast often. As one of his office subtenants, whenever I was in a pickle I’d walk over and knock on his all glass door to talk about it. He and his co-founder, Shradha, hosted dinners and parties and intimate round table discussions, and seemed to always have an extra spot to invite me along. As an impressionable early twentysomething, in Rishi Shah I saw Jay Gatsby, and in me, for some reason, he saw potential.
I didn’t foresee or fully comprehend his meteoric rise that was taking place. And none of us anticipated its spectacular crash. He was simply my favorite & warmest mentor.
In the years since the crash, I’d sent a variety of messages his way. No doubt many others like me were doing the same. General well wishes to try to provide some small encouragement as his storm unfolded in the news. Uncharacteristically, Rishi never replied. I stopped texting.
To that point, when we sat down for lunch in my kitchen, he cut off the small talk to open with an apology. Aside from a small circle of his friends, he explained, he’d withdrawn in those years, and he now regretted it. I echoed an apology on my end that I hadn’t kept at it with the outreach, and that I’d missed the trial while my second son was being born. When he hadn’t replied to the early texts, I didn’t want to overstep or pry, but in hindsight I would have kept checking in.
As the conversation progressed, Rishi had a theme on his mind, a word that he mentioned several times: “lemonade.”
How can I turn my life’s lemons into lemonade?
Trial aside, he’d undergone a personally challenging seven years. After his short stint as the most celebrated new billionaire in town, life had tossed its share of lemons his way. Not my stories to tell. “When it rains it pours” type of stuff, perhaps none tougher than the unexpected death of his father in early 2020.
From a distance, as the articles piled up, I’d sometimes wondered about Rishi’s mental health. It’s one thing to get so-called canceled by college kids on Twitter. It’s another thing to be stamped on the cover of the Wall Street Journal, sued by Goldman Sachs, and indicted by the US Government in a multi-year trial. Verdict aside, at what point does the human spirit crack in the process?
And yet here was this radiant guy sitting across from me in my kitchen. Reflective. Present. Open. Optimistic. Through his dark days he’d grown more spiritual, he’d say. He never stopped reading. Never lost his curiosity for startups and ideas.
We migrated from the kitchen to the backyard. An hour blinked into three.
The oddest part was how naturally the conversation flowed. He’s not my mentor anymore. I’m now several years older than he was in the days when I considered him the wise elder. Yet somehow, as if by nature, in the thread of our conversation he’d occasionally manage to galvanize my belief in myself and the projects I’m working on. Then I’d remind myself that he’s going to prison. But that would feel like a distant reality. He’s still Rishi.
Like many in Chicago, the evolving saga of Outcome Health touched personal chords for me. I’d worked out of their office for over a year. My wife had been an employee at ContextMedia-turned-Outcome for several years, and thus many other employees remain friends of mine as well. When Kasey and I splashed onto the startup scene as the recent college grads airing on Shark Tank, it was Rishi who interviewed us onstage of the packed auditorium at 1871 in March 2014. In September 2017 I’d stood at the podium line next to Rishi, Shradha, and Mayor Emmanuel for the ribbon cutting ceremony of Outcome Tower. And weeks later, on the morning of October 12th 2017, hours before the bombshell WSJ article landed, I was on the phone with Shradha asking her to join our board of directors.
Big stuff to sift through.
But the most memorable times with Rishi were much smaller. Little moments of injecting belief in me when belief was illogical. I retold one of them to Rishi as we lost track of time while sitting in my backyard:
It happened in late 2013. Kasey and I were pitching an investor group composed of the top entrepreneurs in Chicago. I didn’t know much about Rishi Shah at the time, but he appeared to be the youngest person in the group and one of the few to attend our meeting in person. Kasey and I conducted our pitch, and then, by way of a variety of well-reasoned confident voices barreling through the speakerphone on the table, we got ripped to shreds. Not only would there be no investment from the group, but there was an apparent consensus that we were wasting our time by working on Packback at all.
When our disastrous meeting finally ended, I wanted to go bury my head in the sand. Instead, the young guy in the room pulled us aside.
“Hey, do you guys wanna chat for a minute?” asked Rishi.
He led us into a different room and shut the door. Then he did what, over the years, I’d come to recognize as a signature Rishi thing: he completely rejuvenated our spirits, bestowed belief in us, and against the current of his peers’ strongly & intelligently voiced critiques he doubled down on his own pledge for involvement in our entrepreneurial journey.
My raw reaction to the moment, shared afterwards with Kasey, was something along the lines of: dude, that guy Rishi is f***in’ awesome.
I’d require several more pages of this post to recount each of the similar Rishi moments that remain fresh in my mind all these years later. The guy who extends a hand when you’re down; injects belief in you when others doubt. Rishi and Shradha were like our entrepreneurial big brother and big sister.
In the years after pulling Kasey and me into that room to lift our spirits, Rishi’s star rose, and like everyone else in his orbit, I benefited plenty from it. Thinking about those days, I once wrote down in a private reflection that nobody had the juice like Rishi Shah.
That changed in October 2017.
By now we’ve all read the articles and soaked in the coffee shop gossip surrounding them. I’m not here to retell the story of the trial, nor am I dismissing the hurt felt by employees, clients, and investors, or claiming that Rishi’s an angel. Damage was done, and Rishi was CEO.
That the seemingly closest mentee to many of our favorite mentor could be, in the words of the attorneys, a rogue “fraud island”, was not an intuitive trial narrative to process from afar. That the most inviting and articulate speaker of our local startup scene was now silent across social media, private texts, and in court, didn’t mitigate the head-scratching. And his well-publicized expensive purchases would not be considered productive investments towards his public goodwill. For me, left in the multi-year void of Rishi’s voice was a mental question:
Maybe I never really knew this guy after all?
We’re complicated people who crave simplicity. When it comes to someone like Rishi Shah, a former hero whose villainous fate plays out grippingly in the newspapers, it seems like a binary choice of either:
A.) You believe him innocent and love him, or
B.) You believe him guilty and write him off in shame
I’m not sure that the tale of Rishi and Shradha is so simple. In his letter to the judge attesting to the character of Shradha Agarwal, even after having lost his meaningful investment in Outcome Health, Karan Goel emphasized forgiveness: “I say this as a victim of what transpired, but also as someone who believes in forgiveness,” Goel wrote. “The Shradha I knew was always kind, thoughtful, responsive and helpful to others.”
Maybe their story has only just begun.
Whatever happened, there’s no denying that Rishi’s found himself in a heap of trouble.
I know the fundamental feeling. At a much smaller scale, I’ve had my own share of trouble, including but not limited to: suspended for two days plus a month of before & after school bleacher mopping duty for vandalizing lockers with a crayon in high school. A dozen or so disciplinary sessions – before & after school – in the grade school principal’s office. More than one evening detained in the back of a cop car outside of parties that I shouldn’t have been at. Don’t even get me started on the parental-signature-required failed exams throughout.
Yea yea, laugh it up, it’s all small fry distant stuff at this point, I know. But at the time, in each of those moments, the feeling was that of sitting – no, melting — in the hottest seat of the highest authority.
While I’m not condoning or proud of my own self-inflicted moronic trouble, each instance had a hand in shaping me. And to this day each example gives me some degree of credibility when talking with a young person who’s either in trouble, or slipping down a slope of finding themselves in it soon.
My bag of past trouble is the accidentally acquired asset that I now hold in all future moments of mentorship. On that topic, another classic Rishi moment comes to mind:
This one occurred in the prime of his stardom. Having received the city’s highest award for entrepreneurship at a Chicago tech event, he was giving his recipient speech. I wouldn’t have otherwise been admitted into the event, but Rishi & Shradha invited me to sit at their table. The gist of Rishi’s speech was the depiction of a vision:
If every successful entrepreneur could reach out to “pull up” just four other up-and-coming entrepreneurs, imagine what our city could become? He wrapped up by calling the mentality to do so, “Chicago-ness”.
Afterwards, when I complimented him on the speech, he told me that I was “one of his four.”
I’ve never forgotten the vision that Rishi shared that night. Over the years, as I’ve had a chance to give back with my own mentoring time, in the back of my mind I’d sometimes feel a sense of irony that here I was conducting some good deed act of mentoring or coaching that was, in no small part, shaped by the villain I now read about in the newspapers.
A sad ending to a once-promising story? Or …a big juicy lemon?
It doesn’t take a decade as an education industry entrepreneur to know that one of the hardest parts of any effort at youth empowerment is reaching the kids. When it comes to reaching the troublesome kids, there’s something of a paradox at play: the straight-A-never-been-in-trouble adult isn’t necessarily the most well-suited mentor to reach them. But someone who’s felt the hot seat of trouble just might connect.
As counterintuitive as it sounds, maybe the world needs some more been-in-trouble-before mentors in the game.
As dinner time approached and we realized how late our conversation had gone, Rishi called an Uber. We hugged, remarked how good it felt to catch-up, vowed to read each other’s manuscripts, and agreed not to let another seven years go by, no matter where Rishi ends up spending them.
I don’t know what he’ll choose to do in life when all the dust finally settles on his trial & sentence, but I walked away from our afternoon together with a craving to see him (and Shradha) inserted back into the game sooner than later. Rishi was an impactful entrepreneurial big brother to me back in the day. I genuinely believe that, if it’s what he chooses to do, he can be the same for others once again. He appears not to have lost his positive radiance while also deepening his reflectiveness, and now he’s got all sorts of troublesomely acquired lemons to work with.
In terms of one’s ability to be an impactful mentor to help “pull up” the next generation, I wouldn’t be surprised if it once again rings true that nobody’s got the juice like Rishi Shah.