Heidi Roizen

Heidi Roizen | Field Notes
Heidi Roizen | VC Hunted!

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Smashing windows with Heidi Roizen | #VCHunted Twitter Story

When it comes to luminaries in the venture capital space, you don’t have to go far to find Heidi Roizen, a seasoned veteran of the VC game. Frankly, she knew it was all a game from the get-go! Did you know that she created a board game that made national news way back in the day?

Getting through college is merely a game. Heidi Roizen would know. She codified it!

So what is this game all about? Simply put, it was Heidi’s first company with Tim Draper called Draper Roizen Productions. Even many of her colleagues now don’t even know about it! Heidi’s description of how the board game came about revealed to me a lot about Heidi’s personality. She is able to see the meta of her market. She’s able to see opportunities based on patterns and surrounds herself with great people to make those ideas reality. I was super happy that I was able to bring up such a fun piece of history!

I think there is money to be made here… who’s up to make a new game?

Being more on the entrepreneurial side of tech, Heidi considers herself a ‘recovering entrepreneur’ in that:

“Once you have the entrepreneurial spirit, it never leaves you. It’s always what you want to do.”

Heidi Roizen | VC Hunting S2E7
Laughing about the good old days of venture capital and the great relationships we’ve been able to create.

From selling her previous company to trying out the corporate lifestyle, she decided that she wanted to become what she calls a ‘mentor capitalist.”

“A mentor capitalist is where I take my time and my energies and I would devote them to startups but no longer as the CEO, but more as a coach. After a couple of years of doing that I got recruited into venture in 1999.”

Heidi Roizen | VC Hunting S2E7

I found the timing to be precarious. She joined venture capital in May of 1999. This was at the height of the dot-com bubble and I wondered what that was like for Heidi. She recalls that it was great in the first year or so. Lots of money, lots of success. Two of her companies went public and she thought that this VC life was easy! Then the bubble burst and she spent years helping triage, fix, or help companies go under gracefully. Regardless, she certainly got to experience the full breadth and full lifecycle of venture very quickly and she chalks it up to a great learning experience overall!

Giving out a slice of Silicon Valley advice – You should probably subscribe!

One of her favorite lines is: “I’ve been to this movie before.” An to be certain, she has. Her blogs are a great source of information from a Silicon Valley insider. You’ll become a better person for subscribing!

I really wanted to know this story!

I loved watching Heidi describe her experiences with the titans of industry like Bill Gates and Steve Jobs, whom she deems is a national treasure. I also appreciated her first-hand experience verifying that Steve Jobs was also a tough character to work with. 😉

“Your best lessons come from working with challenging people like Steve Jobs, and I wrote the blog post from the perspective of when you are working with someone who is really on top of their game, you really need to know your business backward and forward.”

Heidi Roizen | VC Hunting S2E7

Heidi gave us some real sage advice here. It’s worth listening to Heidi’s recap of how to engage with someone who really knows their stuff. Heidi is clearly a sophisticated investor, where her experiences, her intuition, and her personal insight into how others work has enabled her to rub shoulders with the greats and come out on top.

Click on the picture above to go to the article!

The above article is one that I really wanted to dissect with Heidi. She has such great wisdom in there and I knew that I couldn’t cover them all! Here is the list below:

  1. If you’re not doing something hard, you’re wasting your time.
  2. Your ethics set the tone for your life.
  3. Your gut has more information than you do.
  4. Picking your team is the most important thing you will ever do.
  5. The art of negotiation is finding the optimal intersection of mutual need.
  6. Life is actually really, really random.
  7. Get good at using your time.
  8. The 20-40-60 Rule.

My first question was around #2. I wanted to unpack what she meant when it came to her personal ethics. Heidi’s response was grand:

“Your principles and your ethics, what you choose to live is who you are. I don’t believe that people have one set that applies to work and one set that applies to family and one set that applies to relationships. I believe we are who we are across the board. I bring the same me to everything I do. I am not different. It also dictates who I work with, what kinds of companies I want to be involved in and what people I want to work with because I like to be true to my own values and I don’t want to have to park them and compromise them.”

Heidi Roizen | VC Hunting S2E7
Don’t blame Heidi for being awesome. She’s earned the right!

One thing that I’m a big believer in is listening to your gut. I truly believe that your gut is the amalgamation of your life’s experiences in one place. When I’m working with founders or leaders on a decision, one of my favorite questions to ask them is: “What does your gut tell you?” In my experience, your gut already knows what you need to do. Cut the fluff. Stop looking for validation on other ideas or other options. Go with your gut. It knows. I wondered if Heidi agrees with me here on #3, Your gut has more information than you do:

Shirley MacLaine

“People say that venture capital is all about pattern recognition. There is some value in recognizing patterns but there is also some danger in seeing patterns where there are no patterns. Most of the issues you face in growing and starting a startup are human issues not technology issues. Your gut is informed by all of the history you’ve had and becomes part of your decision-making process and is subconscious. Much of early-stage investing is gut feeling.”

Heidi Roizen | VC Hunting S2E7

I loved the fact that Heidi is a big believer in spending time with early-stage startups to grow a relationship and understand how they’ll respond, react, and make decisions. This is one of those nuances to early-stage investors that I’m particularly passionate about. I find it fascinating that many VCs just don’t spend time getting to know their founders they invest in!

So, what is a wonderful rule for life? I wanted to give the audience some real truth from Heidi: The 20-40-60 rule was my favorite of Heidi’s gems! This is something I talk a lot about to the younger generations of founders and apparently Heidi isn’t the original author of this idea, it’s the actress Shirley MacLaine!

I thought it would be apropos to have Heidi taking a selfie here 😉

“At 20, you’re constantly worried about what other people think of you. At 40 you decide I’m not going to care what others think of me. And at 60 you come to realize that no one was actually thinking about me.”

Heidi Roizen quoting Shirley MacLaine | VC Hunting S2E7

So why does Heidi love this quote so much?

“The 20-40-60 rule is very empowering. I have good news and I have bad news for you and it’s the same thing: Nobody is really thinking about you that much. Even your own mom isn’t getting up every day thinking about you. On the one hand, that means that you really have to look after yourself. On the other hand, it means stop taking it all so seriously! Use your brain cycles for much more important things! The negative self talk in your head, trying to tame that monster is good for your work life, it’s good for your life life.”

Heidi Roizen | VC Hunting S2E7

Such wisdom. Such wow. I love love love it. I hope all of the younger generation founders have a chance to hear Heidi speak on this, or at least read her blog on it!

Girl Power! Heidi Roizen Forbes Entrepreneur of the Year at Threshold Ventures!

It is my hope that as we continue to do great interviews with venture capitalists like Heidi, the younger generation of founders will be able to more deeply understand the people behind the money. All too often the personalities and values of venture capitalists are a black box. It’s almost as if the opaqueness of their character is a strategy. No longer! I’m interviewing the best VCs out there and allowing the world to see who they really are.

I wish Heidi all the best in her future endeavors and I can’t wait to have her on the show again in the future!

Enjoy my retrospective!

Heidi Roizen | VC Hunted Retrospective!


Our #VCHunted Twitter Story for Heidi is the best! Make sure to watch it! [Click above]

Heidi Roizen Social Media

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Heidi Roizen Youtube Quote

Heidi Roizen of Threshold ventures made a game back in the day with Tim Draper! #venturecapital #startups #vchunted #proofofvc

♬ original sound – vchunting

I won’t be forgettin’ that hunt anytime soon!

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