I’ve been in the venture capital industry a long time—getting my foot in the door in the 90’s after a few shots at being the CEO of technology companies. Though they happened to be failed attempts, I’m grateful for the opportunities those experiences presented because they led me to where I am today.

As I’ve paved my path in the investment world, I’ve learned some valuable lessons:

1. Expertise Isn’t Everything

When you first set out as an entrepreneur and start building a technology business, you might think you have to be a technical genius and understand everything better than anyone. This kind of thinking is a significant reason why there aren’t enough women or diverse individuals in the business because they assume they’re not technical enough.

But it isn’t necessary. While the tech is important, not everyone on your team will be on the tech side of things, which might include you too. As long as you have a smart team, it’s all about a consensus of opinion, and having more broad views will get more things done.

2. Build a Team You Trust

Speaking of having a smart team—you want to attract a diverse group with unique strengths. There’s nothing worse than five fraternity brothers or five sorority sisters starting a business together because what do you get when you gather these people who are all the same with the same backgrounds? No new ideas or opinions.

Having a mix of experiences is beneficial as it provides fresh perspectives. Back to expertise not being everything: if you don’t know a lot about tech, then at least you have a team you trust and their backgrounds to make it all happen.

3. Trust Your Judgement

If you’re wondering if something might be a good opportunity or if someone will be a good hire or not, trust your gut. You may be influenced by your partners or lean on the smartest person in the room to sway decisions, but if you’re not making your own views and thoughts first, you shouldn’t be taking others.

There have been moments from my past where I wish I would have pushed my position forward and made decisions that ended up being right. So listen and interpret other thoughts, but stand your ground and compromise after.

4. No One Really Knows What’s Going to Happen

In their humble beginnings, Google was just another search engine and Amazon was an just online bookseller. We had an opportunity to look at Series A for Google back then, but we didn’t know it would become one of the biggest companies in the world.

Through today’s lens, no one could have guessed we’d be navigating a global pandemic. Right now, the market is in a bit of turmoil as investors are slowing down their pace and being more cautious. Without huge IPO or M&A windows, there’s more time to look at deals, making it take longer to raise money. If this continues, this affects everybody.

Long story short: there’s no way to judge any kind of growth. Some people will tell you they can, but nothing is predictable or set in stone.

5. Good Relationships Are Essential

I once landed a deal with two young MIT students by getting on rollerblades. This extremely competitive deal happened in my earlier years when I wasn’t well known yet, and I was up against two other major firms. This turned out to become one of my first ever IPOs because they liked me and wanted me in on the deal—despite struggling to skate from light post to light post on Comm Ave (Commonwealth Avenue) in Cambridge. Was that nuts? Maybe, but building a relationship with them and getting to know them outside of the business made all the difference. 

It’s all about relationships at the end of day. If you want to be part of something—a team or a deal—you have to be on your best behavior and build genuine rapport. From an investor’s stance, unless an entrepreneur likes you, they won’t want to do business with you.

6. Celebrate Small Successes

Venture capital has had terrible times, like in the early 2000s with a bad market and the dot-com world blowing up, or in 2007–08 when the housing crisis occurred. During those times, partnerships weren’t going well, and everyone was worried about how to get out of the ditch.

Then came 2010–2021, where everything has been nothing but up. And yet, we could be in for an adjustment soon. The point is everything happens in cycles, and you get the good with the bad. You have to believe things will get better when at their worst, so emphasize celebrating every little incremental success—they count!

7. Take Time to Help Others

Mentoring and providing others with opportunities is the best part of what I do and the best thing anyone can do. I get a lot of calls from people looking for advice or counsel, and I will always try to spend time with the folks who are honest and open to coaching. Some are recent grads who have no idea what’s next, while others are entrepreneurs who are a little lost.

No matter what stage they are at, it’s worth it if you can help them. After recognizing what you’re good at versus what you’re not, it’s a good idea to give back and share that knowledge with those hungry to hear it and, in turn, feed it back into the industry.

8. Reinvent When Necessary

Some people can survive well by working all the time, whereas others shut down at 5. Regardless of which group you belong to, the question to ask is: Do you like what you’re doing? If you don’t enjoy it, you need to move on.

If someone wants to do the same thing forever, that’s fine if they’re good at it and enjoying it. But if you’re not having fun, do something about it. Why be miserable? You might need to reinvent yourself, your company, the people around you, or whatever is making you hate your job to move on and put a healthy balance back into your life.

9. Think Bigger

Pushing yourself can be exhausting sometimes, but there are no limits to doing what you love. If you have a passion for something, there is no thinking too big, and there are no bad ideas to try. 

The saying, “if you want something done, ask a busy person,” resonates here because you might be up to your neck in responsibilities, but if someone needs you for an opportunity or task or job that only you can do, that makes you feel good. Grand ideas need the right execution to reach success, and if it’s important to you, you’ll make it happen no matter how big and ambitious it may seem. 

10. Fill Your Cup First

You’ll inevitably hit times when you’re overwhelmed and run out of gas, so it’s important to take care of yourself. Do something that doesn’t require mental energy regularly, even daily, to make you feel better and refreshed. You won’t be useful or engaging for anyone—including yourself—if you’re burnt out.

I can’t stress enough about finding what works to recharge your energy. Family stuff, business woes, matters with your significant other—whatever is weighing you down, it’s crucial to figure out what lifts you back up.

Some people enjoy a glass of wine at the end of the day; others need to get outdoors and go for a bike ride after being cooped up for 6 or 7 hours; I like to go for long runs to clear my mind. Alternatively, reenergizing yourself might look like doing something completely different than what you’ve been doing for the last few weeks, months, or years, taking on a new challenge, or exploring a new place.

Whatever you need to do, go and do that as often as you need to take care of yourself and fill your cup.