OP #247: 10 Lessons I've Learned Along the Way

This OP features some excerpts from a talk I'm giving to my alma matter, Skidmore College later this week.

Author

Darren Herman
February 20, 2024

Happy Tuesday OP Community.

✈ I’m in the middle of a quick trip to Dallas to see two portfolio companies: Varsity Brands and Fogo de Chao. Speaking of Fogo, had a terrific meal there with a buddy and my son at the Burlington, MA location this past weekend. Was my first time at this locale and I loved the vibe, the food, and the service. 

❓ Should we do an OP lunch or dinner at Fogo in NYC, Dallas, LA, San Francisco or Boston? If you are interested, please fill out this form. The meal would be free for you as a big thank you for subscribing. I also think it’ll be really interesting networking for those who attend. I’ve never done these before so roll with me.

🎙I had the pleasure of meeting Rudina Seseri when I was at MDC Partners and kbs+ Ventures.  Together, we co-invested in multiple companies and participated on the board of Crowdtwist, which ultimately sold to Oracle. She started her own firm called Glasswing Ventures which was one of the first to go all-in on AI. I listened to a recent podcast interview with her and enjoyed it. If you are into AI, data science, and technology, check out this interview.

📈Congrats to my friends at Bounteous who merged with Accolite earlier this month. A nice combination of the New Mountain Capital portfolio and it creates a wider offering.

✨Nvidia is now worth more than Alphabet, one day after surpassing Amazon (CNN)  I do not know if this trend will continue but… wow.  Nvidia has been on a roll: winning big first in the video game GPU ecosystem, then blockchain, and now, AI. It’s impressive to see a company continue to participate in massive ways to sectors with tailwinds.

If this topic is of interest, you can learn more about what and why AI chips are important:

🚗 For you car lovers out there, did you know the Delorean is back and looks pretty amazing? On the topic of cars, in the last 30 days, I’ve ended up buying one car for my wife and leasing another for myself. I have some thoughts on the process… for a forthcoming OP.

⛳🥒🍹 Last, you have probably heard me talk about Silicon Alley Sports before. It’s an organization that began 17 years ago for senior members of the digital ecosystem in the tri-state area. If you play golf, pickleball, or want to come and schmooze, you can learn more about it here. We just launched ticketing a week ago and we’re 50% sold out for golf and 40% for pickleball. If you are concerned about your skill level and the level of play, watch these videos to get a sense of the group (or reach out to me directly).

Thank you very much for reading. As always, please reach out with any questions or feedback. Hopefully the new Link Colors are more pleasing to the eye (thanks for that feedback, Chad!).

-Darren

Lessons Learned from the Journey - 20 years post Skidmore College

I’m giving a talk to many of the current senior business majors at my alma mater, Skidmore College, this week. I have given a variation of this talk every ~5 years since I’ve graduated but this is my first time doing it via zoom.

The topic is 10 Lessons Learned Along the Way - the “way” being my journey so far.  There are lots of context slides that set up these 10 lessons but I do not have room for those here.  I adapted these ten lessons for the OP, and since most of you are already deep into your careers, they should make sense. If any are confusing or you want more context, please just reach out to me.

1. Passion is your compass, but flexibility is your map. We all have ideas that ignite our spark, but sometimes the greatest opportunities lie in unexplored corners. Be open to detours, because the most fulfilling paths might not be the ones you initially envisioned. 

I was dead set on being a Computer Science major when I came to Skidmore. That lasted one semester. I found other topics I was more interested in and let myself be inspired. 

2. Learn from your stumbles, but don't get stuck in the mud. Bold moves are essential, even if they don't always pan out perfectly. Embrace the bumps as learning experiences, dust yourself off, and keep iterating.

At IGA Worldwide, we took big swings but the market didn't play out as quickly as we anticipated. We had to embrace the bumps and interate as we went. Change was constant.

3. Knowledge is power, but connections are your support system. Data provides valuable insights, but the human touch is irreplaceable. Build genuine relationships, not just a network of contacts. Remember, even the most sophisticated algorithm thrives on meaningful connections.

One of my largest successes - both as a business and financial gain, was building Varick Media Management. In order to do this, there were plenty of folks behind the scenes such as Joe Zawadzki, Nat Turner, Brian O’Kelley, Erich Wasserman, Jenna Griffith who inspired and made it happen with me. Without their support - and at times 24/7 - we would not have accomplished what we did.

4. Lend an ear, share your voice. The best leaders are active listeners, not just charismatic talkers. Absorb diverse perspectives, challenge your assumptions, and unearth hidden gems of wisdom buried beneath mountains of opinions.

It’s amazing what happens when people talk: and continue talking. They end up saying something dumb 75% of the time.  That number isn’t scientific but usually, the person who keeps talking ends up going down the wrong path.  Listen more than you speak, make no assumptions, and hear all voices in the room.

A very famous creative director and agency owner I used to work with used to say, “a good idea can come from anywhere and anyone.” Be that person who enables that type of thinking.

5. Value isn't a hashtag, it's your guiding star. Don't chase trends – solve real problems. Create something that makes a positive impact, something that truly serves people and inspires them to invest. That's the sustainable magic that fuels long-term success.

It’s not that hard: add value. Finding ways to add value to a conversation or business is not difficult and often, it can be lots of little ways that end up creating the ultimate value. Do not think you need to solve everything… adding value simply is often the best.

6. Your career is a choose-your-own-adventure. Forget rigid plans and predictable trajectories. Embrace the unknown, pivot when necessary, and rewrite your story as you go. The only constant is change, so befriend it and see where it takes you.

Your life is a book.  Each chapter is written as you progress. Think of your career as a set of unwritten chapters that only you get to write. Embrace that. And own it.

7. Data is fuel, but creativity is the engine. Don't let spreadsheets dictate your vision. Use data to inform your decisions, not dictate them. Be the maverick who bends the numbers to your will, not the robot blindly following algorithms.

Leveraging data is important to any decision you will make. With that said, the data will help you unlock creativity. Do not feel that data will limit your creativity. If you feel limited, try and get even more creative.

8. Show up, even when you feel like an imposter. Authenticity is more powerful than perfection. Roll up your sleeves, get involved, and embrace the journey. The world needs your unique blend of passion and dedication, not another polished persona.

Being at the table or the event is 90% of the battle. Most people avoid it.  Just show up - and when you do, apply yourself. Often, I find that the connection I make may not be immediately impactful but down the road, it absolutely is.

9. Momentum is your ally, stagnation your enemy. Keep moving forward, even if it's in small steps. Celebrate milestones, learn from setbacks, and don't let doubt hold you back. Remember, even a snail eventually reaches its destination.

Nothing is better than getting momentum and riding it. It helps a team believe. It helps build market presence. It has an incredible way of turning prospects to customers. Keep moving forward.

10. Trust your gut, even when it whispers softly. Intuition is a powerful tool honed by experience and instinct. Learn to decipher its messages, even when they seem counterintuitive. Sometimes, the loudest voice in the room is the quiet one within.

There are so many times in my career where I doubted my gut and ended up having to course correct a few days, weeks, or months later.  Trust yourself.

I hope these were helpful. I’m not big on giving “guidance” or “advice” but since I’m talking to the Skidmore seniors, I figured I’d share it here for all of you too. I hope you enjoyed.

I've done extensive reading this week and I hope you'll enjoy the following links that I've curated. If you come across an article that you believe would be a great addition to future OP letters, don't hesitate to share it with me. However, please note that I retain the discretion to decide on the content that goes into each OP letter.

Thank you for reading!

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