Does anybody know what time it is?

The year is 1994. Seinfeld is the top TV show, George Clooney is becoming a star on the 2nd most popular show (ER), and Forrest Gump is the top grossing film. However, The Lion King (2nd highest grossing film) and Home Improvement (3rd most popular show) had a big cultural significance. They also had one common thread - Jonathan Taylor Thomas, aka Jonathan Weiss…better known simply as “JTT.”

JTT was everywhere in the mid 1990s - from all the teen magazines, to popular shows/movies, and posters hanging on most teen girls’ bedroom walls. Although he was only making $8,000 per episode (roughly $17,000 in today’s dollars), he was potentially as popular as Tim Allen. It seemed like JTT was bound for big things.

Four years later, JTT starred in “I’ll be Home for Christmas” alongside Jessica Biel. And…basically disappeared from acting. 

I have never watched the Lion King (probably will with my son at some point), but did recently stream I’ll be Home for Christmas. While I did watch Home Improvement as a kid, I’ve never had a JTT poster on my wall, or followed his career. 

I tend to just let my mind wander when I’m looking for new writing ideas. Often times, I’ll listen to music and just surf the internet, looking for things that trigger my imagination (and fit with a venture capital related topic). In this case, it was 2:30 AM, I was falling asleep, and needed some background noise. While Forrest Gump is my dad’s favorite movie (and in my top 3 or 4), it was Christmas time and snowing…I’ll be Home for Christmas looked mindless enough for me to think about other things. In this case, it went from background noise to my focus for the night. 

JTT was Randy Taylor for 8 seasons (178 episodes), Young Simba’s voice on the Lion King, and even Tom Sawyer on “Tom and Huck.” By 1998 (Season 8 of Home Improvement), JTT was likely set for life, and primed for a big acting career. While JTT did make it home for Christmas (actually not a bad movie), he fairly quickly faded into the background. 

It’s very rare for someone - in acting, music, or the normal business world to quickly shift from the big spotlight to quietly exiting out the side door. When you’ve worked so hard, showcased either amazing timing or talent, and reached fairly rarified air - very few people can just walk away. The offers to continue in the same field are too tempting. And, the thought of making it so far, and so high makes it very hard to simply walk away. There are countless talented young people desperately trying to break into something, anything in Hollywood each year. Once someone has broken through to the top, especially at a young age, it’s almost unfathomable to give it all up. 

However, JTT did exactly that - and enrolled at Harvard in 2000. He didn’t study film, or business - and instead focused on history/philosophy. While he ended up graduating from Columbia and is on the SAG-AFTRA board, he’s only had very limited cameos since the late 1990s. 

So, what’s the possible VC tie-in to a 1990s teen heartthrob who quietly walked away near the top of the business? 

There are a few places to take this newsletter - but the most obvious (to me) is with founders. Each founder’s mountain is different - some dream of summiting Everest, some dream of summiting Mount Whitney, and others dream of summiting their local mountain (or hill). In many cases, it’s a downright crazy, complex, and all-consuming hike. Once they hit their summit, many struggle to make sense of it all. VCs are usually pushing them to keep climbing (for a bigger exit or to take on more funding). Spouses and loved ones are usually (not always) reminding them that they are in fact, on the summit (and should take in the view for a while). And, their co-founders are either very happy, or pushing to hit the next (taller) summit. 

Every situation, company, and founder is different. Going bigger is not always a bad thing. And, not all VCs are mindlessly pushing for bigger mountains and riskier exits. However, I find myself regularly reminding founders that they have reached their summit - and can slow down. That it’s OK to recharge a bit, OK to sell the company, and that they’re not necessarily leaving huge money on the table. $100m exits can be great. So can $20m, or $30m exits. Most companies and founders are not destined for huge exits, and lottery sized checks. But, many strong founders can exit with fairly life changing money, their sanity, and marriages intact. Bigger can be better - but exiting on your own timeline and terms can sometimes be best. 

In JTT’s case, I’m sure he could ride the 1990s nostalgia wave back into Hollywood, and have his pick of acting jobs. However, he had his exit in the late 1990s, and reached his own summit. While he could have tried for Everest or another huge peak, he reached his point of happiness, and walked away on his own terms. I wish more founders knew that it was OK to do the same thing - and that (good) VCs would understand. 

I’ve had some recent portfolio exits myself - none were huge, and none really moved the needle. But, the founders reached their summits, delivered good returns, and walked away happy. It’s my job to maximize my own fund returns for my investors, but it’s also my job to help founders. Both can be at war with each other at times. However at the end of the day, maximizing returns also means maximizing where a founder can take the company - if it’s a smaller summit, that’s where the trek needs to end. 

Not every company can be a unicorn. Not every founder can have a giant exit. And, it’s my job to know where the company fits within a portfolio. Some of my founder’s will be JTT, a few will be more like Dustin Diamond, and very few will be like George Clooney. While the George Clooney’s of the world will get all the press and all the attention, a fund manager can do quite well with a portfolio full of JTT-like founders. In many ways, those are the founders I’m backing - talented, hungry, and knowing when to exit (often much earlier than other venture funds).