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One Investment Leads to Another

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Photo: Aaron Pergament Photography

Any aspiring entrepreneur would happily take a meeting with Ludlow Ventures a venture capital firm located in downtown Detroit.

On a typical day hundreds of unsolicited e-mails arrive in company inboxes and Ludlow’s schedulers are busy setting up meetings with eager entrepreneurs who hope Ludlow will fund their dreams.

And if they make it through the doors one of the first faces they’ll see is that of Jonathan Triest a 34-year-old venture capitalist who runs the company with partners Brett deMarrais and Blake Robbins.

“I have the attention span of a gnat which gave me trouble growing up but this line of work with the vastly different businesses and personalities I meet lends itself well to my personality ” says Triest.

These days Triest is funding entrepreneurs to the tune of millions of dollars annually. From his post-modern offices in Detroit he’s bet on more than 100 companies already among them in-car heads-up-display device Navdy; Honey an app that scours the Internet for coupons and discounts; and Notarize.com an application that allows consumers to connect with a notary public by live video or via their mobile device.

But it’s his newfound love — Torah — that keeps him grounded and his priorities in order. And he knows that success in business could never come without blessings from Above. “It’s now abundantly clear to me that everything in my life both personally and professionally both good and bad comes from Hashem.”

What I Learned in Yeshivah

The Ludlow office in downtown Detroit is hip and inviting with funky art on the walls and half-painted half-exposed brick décor. Out-of-the-box thinking is encouraged — part of the reason there are orb-shaped swings hanging from the ceiling and a ping-pong table set up for an afternoon game. The temptation for constant fun can have its downsides though; Triest admits he sometimes leaves the office to find a quiet space to work.

Triest who started Ludlow in 2009 after receiving a generous start-up loan from his father Brent Triest and great-uncle Warren Coville has set his firm apart from the others by emphasizing personal relationships with his clients. Ludlow has even passed up tempting investment opportunities because the personal fit didn’t work. “We always say it’s like going on a road trip with someone. Here it’s going to be a long journey — some as long as ten years or so — and we want to like the people in the front seat.”

Triest likes to push the envelope. At a technology conference in San Francisco in October 2016 he spoke to a packed audience of business executives on the subject of “Everything I’ve Learned about Building a Strong Company Culture I Learned in Yeshivah.”

Despite initial skepticism (“What’s yeshivah?”) the attendees — some of whom were Jewish but most of whom were not — listened as Triest described the importance of taking a weekly break from the daily grind and avoiding the number one destroyer of any company culture — gossip.

He also told his audience that great leaders admit their mistakes and provided examples from the great Torah sages of the Sanhedrin who encouraged the most inexperienced members to share their opinions first before their viewpoints could be swayed by senior opinions.

As a kid Triest was kicked out of Hebrew school — more than once. But to hear how this young successful venture capitalist became who he is today perhaps we should start from the very beginning

Jewish Was a Good Thing He paints a picture of a warm, happy childhood with 16 siblings (“Really?” I ask. “Nope, kidding, just one sister.”) growing up in a Reform household in Huntington Woods, Michigan. Life was good. His parents sent him to public school and Hebrew school, where his typical adolescent chutzpah was not appreciated.

“Even though Hebrew school was not important to me,” Triest says, “I always had this vague Jewish pride. I couldn’t tell you what that meant — or even where it came from — but I knew I was Jewish and it was a good thing.”

Triest’s father began learning Torah with Rabbi Eric Krohner of Ohr Somayach, who’d turned up at his office door during a fundraising campaign. The senior Triest, a veteran lawyer turned investor, enjoyed a good argument, particularly about philosophy, and after some whammies with Rabbi Krohner, found that some Torah ideas had stuck.

While Triest was in high school, his father started taking on mitzvos, though he never pushed anything on his family.

“Now, as a parent of three kids, I recognize how brutal it must have been,” Triest recalls. “He’d walk a mile and a half to the Detroit Kollel and then back a mile and a half home, where the rest of the family was not keeping Shabbos. The contrast must have been so difficult for him.”

The teenaged Triest was happy with his father’s Shabbos observance — it meant he had his father’s car at his disposal on the weekends.

After graduating high school, Triest attended the University of Michigan.

One day during his junior year, he happened to bump into Rabbi Aaron Dovid Eisemann, who was asking students in the center of campus whether they were Jewish. Triest happily said he was and “Rabbi E” explained he was offering a stipend for students to learn Torah.

“He didn’t lead with that, but that’s what I came away with,” says Triest, who was happy to accept the offer, figuring he could tune out during the two-hour class and still have an extra $50 in his pocket.

He attended the classes, and in the meantime began accepting invitations for Shabbos meals at the homes of community members, including the program’s founder, Rabbi Avraham Jacobovitz.

“At first, it wasn’t the ideas but the people that struck a chord,” Triest says. “I was blown away by the families, the way they interacted with each other. I come from a loving home, and my parents are wonderful, but my own kibbud av v’eim was lacking. I would have done anything to get out of doing the dishes at home, but here were kids, barely nine or ten, clearing the table, helping guests they had never met.”

Further inspiration came from meeting successful frum businessmen who were educated in both the religious and secular worlds. A pivotal moment came after class one day when Triest returned to his house on campus and started to look for something to eat. He mechanically headed over to his roommate’s shelf and was about to help himself to his cookie (“I’d reimburse, or more likely not”) when a strange thought occurred to him: he was stealing. Even if it was only worth ten cents, the potential ramifications were far greater.

“I know it sounds trite,” Triest acknowledges, “But I was taken aback by my own thinking. That’s when I realized that all that hashkafah was starting to permeate my life.”

One morning during his senior year, Triest woke up with terrible back pain and soon found himself in the ER with a kidney stone. Desperate for a quick fix, he called Rabbi E.

“I asked him for a secret blessing to make the pain go away,” remembers Triest.

Rabbi E replied that Torah is not voodoo but suggested taking on a mitzvah in the merit of a speedy recovery such as reciting the brachah of asher yatzar.

“It was like naaseh v’nishma,” Triest laughs. “I said, ‘Yep, yep, no idea what that means, but I’ll do it.’ ”

At the same time, he also committed to putting on tefillin daily. Although recovery was slow, Triest said the experience filled him with a newfound appreciation for the healthy functions he’d always taken for granted. Still, beyond that he didn’t commit to changing his lifestyle or taking on more mitzvos.

In 2002, Triest was one of 15 students graduating from the Jewish Resource Center, an event at which parents were invited to attend and each graduate spoke. After hearing the speech of one young student, Jessica Leeb, Triest’s father leaned over and whispered in his wife’s ear, “I bet you that’s the girl Jonathon marries one day” — a prediction he would proudly share five years later, at Jonathon and Jessica’s wedding.

Post-graduation, Triest moved to New York where he worked in advertising and marketing for a number of different organizations. Despite being in one of the world’s biggest Jewish metropolises, he missed the easy access of his hometown Jewish community and felt disconnected.

An opportunity to connect presented itself one day in a bagel shop, when Triest noticed a gentleman in a kippah. “I wanted this man to know I was Jewish, so I turned to him and said, ‘Excuse me sir, do you know when Shabbat starts?’ Triest recalls. “He said, ‘It probably starts around 6, but I don’t really know yet, because… it’s only Tuesday.’ ”

The man, Marcus Lehmann of Brooklyn, struck up a conversation, and soon the two were learning together weekly.

Soon after that, Triest attended a Purim party organized by a kiruv organization for hundreds of secular young professionals. Running late, Triest arrived in the middle of Megillah reading, after which he sought out the rabbi to thank him, saying enthusiastically, “That was beautiful, thank you so much; hopefully next year I’ll hear the whole thing.” The rabbi explained that actually the mitzvah was to hear the entire megillah, and not just half, to which Triest replied, “Ah, well, hopefully next year.” He was completely taken aback when the rabbi offered to read it again, just for him — a complete stranger — before he’d even broken his fast.

The next day, a similar thing happened: Triest was running late yet again, missed half of Megillah, and called Lehmann, who urged him to jump on a train to Brooklyn and head over to his house, where he’d lein for him, despite the late hour. “Both incidents, which occurred in less than 24 hours, clearly illustrated an important point — besides the fact that I’m obviously fantastically disorganized and always run late: Jews are willing to go far out of their way for other Jews, for the sake of a single mitzvah. I was very moved.”

As it happens, Triest got a job doing design work for Discovery Productions, a division of Aish HaTorah, and had an opportunity to observe religious Jews up close. He was particularly impressed with the frum women he met, who seemed to have clear spiritual goals and weren’t caught up in the mundane aspects of life. “At the time I didn’t know the word ‘chein,’ but that’s what I saw,” Triest says. “That’s when I recognized that I wanted to marry a frum woman and have a frum family. I, however, did not want to be frum myself, so I figured I’d just have to hack the system somehow.”

He shared this plan with his mentors, Rabbi E, Lehmann, and Tom Steinberg, a successful businessman who was introduced to Triest in his early days during his New York job search. The three managed to explain why it wasn’t feasible, and that’s when, together with a dawning conviction of the emes of Torah, Triest decided to take on more mitzvos.

The trio also helped convince Triest it would be a good idea to attend yeshivah, but he avoided making a commitment. He had even chosen a yeshivah, Machon Shlomo in Har Nof.

“I told a coworker at Aish I wanted to go to yeshivah, but it was too expensive,” Triest recalls. “Next thing I knew, I was called into the director’s office. The director, Rick Probstein, said, ‘It took one team e-mail, and 30 minutes, but we’ve raised all the necessary funds for your trip.’

“I said, ‘I guess I’m going to yeshivah then.’ ”


G-d Understands

Duly enrolled, Triest was soon on a plane. That’s when reality hit. “I thought, ‘This is crazy. What am I doing? I’m doing fine with minimal mitzvos. G-d understands. My family, friends, life, everything’s great. I don’t need yeshivah,’ ” Triest remembers. “It was a frustrating realization because it occurred as I was sitting down in the airplane seat. I started looking for ways to get off the plane without getting arrested. Could I fake a heart attack? Pretend there was a fire?”

Clearly agitated, he aroused the concern of his seatmate, a white-bearded gentleman, “who looked like a typical Jewish grandpa.” The man, who introduced himself as Noah, asked if he could help in any way. Triest promptly confided his reservations and fears. In response, the older man put his arm around Triest, and, as the plane started off down the runway, shared, in Triest’s words, “the most wonderful, warm Torah, so deeply penetrating and well-articulated, it immediately connected to my nervous system that had been firing so erratically just moments before.”

As he spoke, Noah smilingly pinched Triest’s cheek, prodded him, and patted his face. “I’m this punk, young kid,” Triest exclaims. “If someone’s going to pinch me, I’m gonna do it back, so there I was, pinching him, poking him, tugging his beard. We’re joking around, having a great time.”

A few hours into the flight, a man sitting a few rows behind Triest tapped him on the shoulder and asked to speak to him. Triest followed him to the back of the plane where the man said politely: “I don’t mean to disturb you, but that man you’re poking and pinching? He’s Rav Noach Weinberg, the rosh yeshivah of Aish HaTorah in Jerusalem. Basically, he’s a really big deal, so maybe you should stop?”

As he inched his way back into his seat, Triest whispered, “Excuse me, Rabbi,” and Rav Weinberg, realizing the jig was up, asked with a smile, “Who outed me?!”

“Poor guy, he gets on the plane, probably looking forward to the only solace he’ll have in weeks — and then he gets me!” laughs Triest, before turning serious. “Still, it was clear evidence Hashem was guiding me; the hashgachah was obvious. In my deepest moments of anxiety, Hashem put me right next to one of the greatest Torah giants of our generation.”

For the following two years Triest studied at Machon Shlomo under the guidance of the rosh yeshivah, Rabbi Beryl Gershenfeld, where he grew in his observance. In 2006, he returned to the States, where he reconnected with his old college friend Jessica, who’d independently followed a similar journey to Torah.

After marrying, the couple settled in Atlanta, where Jessica attended medical school at Emory University, and they welcomed their first child, Shayna, now seven.

In 2009, they resettled back in the Motor City, where they have since been blessed with two more children, Aryeh, now five, and Eliana, now two.


Every Step of the Way

And now it’s come full circle. Triest is no longer accepting money to learn Torah, but sponsoring a weekly shiur in his office delivered by Rabbi Leiby Burnham, of Detroit’s Partners in Torah. Whether he’s learning or exploring the latest tech venture with his business partners, Triest is filled with a deep appreciation for the path Hashem has led him on.

“I’m well aware and so thankful that Hashem has been with me every step of the way, from meeting Rabbi E, my wife and Reb Noach, all of it. Last year, I was asked to be president of the Jewish Resource Center, where I assist the current director, Rabbi Fully Eisenberger, who works day and night for the students. This is the very program that started me on my own journey, and I love having the opportunity to help it grow.”

In other words, one investment leads to another.  —

7 things you should know before approaching a venture capital firm…

Ideas are exciting, but everyone has good ideas. There’s actually very little value in ideas — but there’s lots of value in execution. Do you have the ability to actually create a product? Bring an idea to fruition? Even if it’s a half-formed, early-stage, bare-bones prototype, the fact that you’re demonstrating you can execute an idea goes a long way. We like to see people say, “I was bothered by X, so I started making Y. It’s nowhere near completion, but this is what I have so far.” That shows us it’s more than just an idea.

When we do meet, if you don’t know something, just say “I don’t know.” When an aspiring entrepreneur answers every question with great confidence, it sometimes looks like they’re just blowing smoke. When someone is comfortable saying, “I don’t know,” it makes me trust that all their other answers are honest and legitimate. Saying “I don’t know yet” shows you recognize you aren’t perfect. Venture capitalists will sniff out when you’re making something up anyway.

The truth is that we like to seek out our own entrepreneurs, although we have invested in some that have reached out to us themselves. We hear from thousands of people a year, and after a while, they all start sounding the same. The best way to get to us is to find a common connection. If a reputable source tells us they want to introduce us to someone up-and-coming who they personally recommend, we’re likely to take that seriously.

You can’t find a common connection? No problem. E-mail us. However, we get thousands of e-mails, so you’re going to have to find a way to make yours stick out. Do not start with “Dear Sir/Madam, Please look at the following opportunity…” That’s how they all start, and it’s boring! I’m more likely to continue reading honest, concise e-mails. For example, “Hi, I tried to find a common connection, but couldn’t. I recognize this is a long shot, but here’s what we’re working on…” I always appreciate honesty.

Be creative! Someone once sent us home-baked cookies with a handwritten note that said, “I made these with $3.50. Imagine what I could do with a lot more money!” She did it; she had our attention. We got in touch with her, heard her out, and were impressed, although we ended up not funding her for other reasons.

Keep it short. Don’t send me your 400-page business plan unless I ask for it. I’m not going to read it.

Show us your passion. We love to see people’s excitement about what they’re working on, how they’re always thinking about their product and trying to make it better. It’s a great sign when there’s a personal reason behind the passion, rather than just “I had an idea and want to make lots of money.”

(Originally featured in Mishpacha, Issue 648)

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