Wendy Lea talks about the risks of saying no

Entrepreneur, investor, and Techstars board member Wendy Lea remembers the beginnings of Techstars, her first encounters with #GiveFirst—and how mentors have changed her life.

Wendy Lea is a longtime entrepreneur and investor, as well as a board member and mentor at Techstars. With David and Brad, she digs into some of her first mentoring experiences and reflects on a time when a mentor changed her life.

Wendy was early in her career and had just been offered a promotion that would cause a lot of change in her life, and she was hesitating. Her mentor told her: the risk of saying no is very high. “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential.”  

She did, and she traces her success back to that encouragement and good advice.

Listen for more about the risks of saying no… and saying yes.

Bonus: Listen to Wendy, David, and Brad reminisce about the first Techstars class.

Subscribe to the Give First podcast now.

Companies and resources mentioned in this podcast:

EventVue – closed

First Round Capital

Cintrifuse

Get Satisfaction – acquired by Sprinklr

OnTarget – acquired by Siebel Systems

Pipeline Equity

Siebel Systems – acquired by Oracle

Small Fry, by Lisa Brennan-Jobs

SPCA

An edited transcript of the conversation follows:

David: We’re really excited to have Wendy Lea here as a guest today on the podcast. Wendy is a board member at Techstars, and she recently moved back here to Boulder after spending four years in Cincinnati as the CEO of Cintrifuse. Welcome, Wendy.

Wendy: Thanks a bunch. That was a fun gig by the way, Cintrifuse. I’ll end on that.

David: Spend a few minutes giving us your origin story.

Wendy: A little bit about my background might help those of you listening grok my experiences and where they come from. My big success came with a company called OnTarget, and it came after lots of professional training in large companies. With OnTarget, three or four of us worked like dogs to make that work around the world. We owned it 100%, and we sold it for $150 million to Siebel Systems in 1999.

After that, I worked for Siebel, which was fantastic. I loved that because I learned a lot, and then I took that experience and started doing new things with it, for example, really working with venture-backed startups. That was very different: the risk, the reward, and the kind of mentoring that startups required. It was this that brought me to Boulder. In Boulder, I worked with companies like Lead Works—formerly Duo—and also Numerics.

Then I went to California. I made a bunch of angel investments and I did a big tour of duty at Get Satisfaction. Get Satisfaction was a big love, my biggest love in all of my work life. It didn’t turn out as planned, but it was quite remarkable. I’m back here in Boulder now, and proud to serve on the Techstars advisory board.

Brad: Wendy, would you talk a little bit about how you got introduced to Techstars and what your involvement with Techstars has been?

Wendy: At the very beginning it was an ask from you to plug into the community. From there you introduced me to David, and David told me about his big idea about bringing entrepreneurs and mentors together. That’s the first time I heard about Techstars, and that was the first cohort. I’ve hung around with a lot of mentors, and I became plugged in through the community that Techstars created here in Boulder.

David: Back then, that was really the first super visible example of Give First in Boulder. There were so many mentors who were trying to help that first class of 10 companies—which turned out to be a great class—and get this whole mentorship-driven accelerator thing going.

Tell us about your biggest lesson as a mentor.

Wendy: My biggest lesson as a mentor was with a company called EventVue. The founders, Rob Johnson and Josh Frasier, had an idea that was completely easy to understand. It wasn’t complex and crazy. I really got it and I liked what they were doing.

They were very, very early in their life cycle as entrepreneurs and they were impressionable. If a mentor told them something would work out, they really believed it. It was a struggle because I didn’t want to dispute other advice they were getting, but I suspected that the situation wasn’t going to work out. That was tricky, because you want to be upbeat. I believed in what they were building, and they were working like dogs. Of course, it didn’t work out.

Now when I see them, they always say, “Oh, I’m so embarrassed when I look back and think that I was so cocky.” And I say, “You know, it happens.”

David: So you were trying to manage that dynamic.

Wendy: I was trying to manage their expectations. This was before all the cool modules that we have now in mentoring, it was just us bushwacking through, doing what we could to give back. It was tricky. I did what I was taught as a young woman: ask a lot of questions, and see if they’ll tune into that reality or not.

Brad: Wendy, you’ve been involved in lots and lots of companies, both as a founder or entrepreneur, and you’ve been brought in by a bunch of startups to help by serving on their boards. You’ve also been a startup investor. When you reflect on all of those experiences, what’s the most fun you’ve had with a company?

Wendy: Building out the leadership teams.

Brad: Can you talk us through an example?

Wendy: On the venture backed side, it was awesome building out the team at Get Satisfaction. It was also hard.

Brad: What were some of the awesome things?

Wendy: We were really trying to figure out the match between the skills and knowledge that were being represented, and the needs we had on the team. We hired someone, and it turned out we brought in the completely wrong person.

He didn’t know how to get his hands really dirty: sit with the engineers and talk with them directly about what they saw in the code. The code needed to be refactored. It was going to be an expensive proposition. We all kind of knew that, but the guy was saying all the right things. He affiliated more with the product managers, and not with the engineers, and it caused problems.

That was a significant turning point for me, because I don’t have that background. I had to listen and learn and ask the founders. It was exciting and scary and costly when you did it wrong. I made a big mistake there and it really cost the company a lot of time and money.

David: Yet it was awesome.

Wendy: It was awesome.

David: Sounds like you learned a lot there.

I’m curious if you have an example from your career, Wendy, where somebody gave you some advice early in your career that really changed a lot for you?

Wendy: I’ve got one example from early in my career and one from later.

I had an opportunity as a young woman, in my mid-twenties. I got a promotion that required me to move from Jackson, Mississippi to New Orleans. It looked very risky to me. Personally, I’ve gone through a lot of change, so I can deal with personal risk, but I like my professional life to be stable. I was worried about moving and not knowing anyone in New Orleans. My husband couldn’t move with me.

My mentor, who was one of my bosses at the company, said to me, “The risk of saying yes is really very low. The risk of saying no is very high.”

I didn’t get it. My brain was going crazy. He told me, “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential. So you don’t know anyone. You’ll meet people.” I’d never thought of that: the risk of yes versus the risk of no.

I told my husband I was moving to New Orleans. Of course he didn’t come. Yes, there was a divorce. Life continues. But that comment about playing small really made me think, and taking his advice changed my life.

The other advice, from later in my life, was from Rob Hayes, who’s a very dear friend at First Round Capital. He was an investor in Get Satisfaction when one of our first term sheets was pulled. The company had no money. We had zero. We were funding it ourselves, we weren’t doing well, and the term sheet got pulled. I didn’t know to be upset about that. I had not had enough experience to freak out when this happened.

Rob understood what it meant, and we met at a coffee shop. He asked me what we were going to do, and I told him that we would keep looking for money and I would invest and we would keep going.

I loved this company, and he was just like, “Wow.” Then he said: “I support you.” For Rob, if I thought there were conditions that we could build around, he was going to support me.

Brad: In 60 seconds or less. What does Give First mean to you?

Wendy: Give without expectation of return.

David: That’s far less than 60 seconds. I’m going to start using that.

The other thing I’d love to hear about is an example in your life where you’ve seen the power of Give First in action.

Wendy: There are lots of those! Here’s one. I was working with some universities in Cincinnati, and we were doing a coaching workshop, teaching people how to do good coaching or good modeling, showing behaviors by doing them. We were working one day in the engineering school, in a coding class. One of my students went over to a young woman and sat down with her. He said to her, “I can tell you’re struggling with this. What can I do to help?”

No one told him to do this, and I didn’t instruct them to run around the room and help each other out. That was good observation and good modeling. I’m really proud of that. It was very natural, so she didn’t feel awkward.

The more we model this behavior—giving without keeping score, and without needing immediate reciprocity—that will change the scope and slope of the work we do. If you model it suddenly and set expectations suddenly, then people lean in. They learn how.

Brad: That’s great. The last section here is something that we lifted from our friend Harry Stebbings, a quickfire round. We’re going to ask you a handful of short questions and we’d love very, very fast answers to each one of them.

David: Let’s do it. Wendy, what’s your favorite book you’ve read in the last year?

Wendy: Small Fry, by Steve Job’s daughter Lisa.

David: Do you have a favorite charity you support?

Wendy: I support the SPCA because I’m a big dog lover.

David: Tell us about a startup you met recently that you think people  should check out.

Wendy: I’m very excited about Pipeline Equity, which happens to be a Techstars company, led by Katica Roy.

David: What’s a city that you think people have to visit before they die?

Wendy: I would say Oxford, Mississippi.

David: You did it. You’re through it. Thanks for joining us, Wendy. It’s been a blast having you.

Wendy: My pleasure. Thanks for having me.








Why Make A Give First Podcast?

Today, I’m excited to announce the launch of the very first podcast from Techstars: the Give First podcast. Brad Feld and I are co-hosting this weekly podcast that digs into what Give First means.

I can tell you that I’m having a great time making it, and I’ve already learned so much from the people we’ve had as guests.  

What is Give First?

Give First is one of our core values here at Techstars. It means helping others with no specific expectation of return. It’s not transactional—it’s the idea that if you’re helpful, it will come back to you in completely unexpected ways.

Why Make a Podcast?

This is great, but I know it can sound a little abstract if you haven’t experienced it yourself. You may be wondering if it really works. Do busy people—and entrepreneurs are notoriously busy people—actually stop and Give First?

Yes, it really works.

I hope that you listen to the Give First podcast for insights into how exciting and successful a life and career guided by the principle of Give First can be. Here are just a few examples from the first few episodes:

  • Hear Paul Berberian, CEO of Sphero, tell the story of being mobbed in Times Square like a rock star when Sphero’s toy BB8 was the number one toy in the world.
  • Listen to Wendy Lea talk about the risks of saying “no” when opportunity comes knocking.
  • Troy Henikoff tells a decade worth of Give First stories that all intertwine—and resulted in companies growing, careers thriving, and millions in funds being raised, all while the Chicago startup ecosystem is expanding.
  • Mary Grove shows the power of Give First at scale, with her adventures in community-driven change, starting Google for Startups and traveling on the Rise of the Rest bus.

Like I said, Brad and I are having a blast making the Give First podcast. We get to have fascinating conversations with accomplished, generous people. But most of all, Brad and I are making this podcast as yet another way to Give First. We hope that by sharing these stories with you, you’ll be inspired to Give First as well.

Listen now to our introductory conversation, where Brad and I talk about where the idea for Give First came from and what it means to each of us. And subscribe to the Give First podcast!








The Twenty Minute VC with Moisey Uretsky: Founding DigitalOcean, Making Mistakes and Scaling a Love Culture

Moisey Uretsky is the Co-Founder & Chief Product Officer at DigitalOcean (Boulder ‘12), the second largest and fastest growing cloud computing platform.

I recently had the chance to join Harry Stebbings on his podcast, The Twenty Minute VC. Click here to listen to the episode to learn:

1. How DigitalOcean came be the second largest cloud computing platform.

2. I’ll explain my quote, “’We did everything wrong for a decade.” What were the biggest mistakes I made and how did I look to rectify and learn from them?

3. My thoughts on if / how one can learn to be a great business leader. Is it inherent or if not, what are the steps required to increase your chances?

4. How does DigitalOcean fundamentally scale love? What are the inherent challenges of building this type of culture? How does the theme of love play out in the hiring and the onboarding process?

 


The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. It helps you discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded.







The Twenty Minute VC with David Cohen: Investing in Uber, Twilio and SendGrid

I love the 20 Minute VC podcast. It’s the perfect amount of time and Harry Stebbings does a great job attracting interesting guests and asking them the right questions. I was honored when asked to be on the show, here’s that episode.

Harry asks me questions like:

  • How did I make the transition from Founder to VC with Techstars and Fund I?
  • Fund I is one of the most successful funds in history; what was the structure with Fund I? Why did you choose a $5m fund size? How did you decide initial to follow on ratio?
  • Why were you so valuation sensitive with Fund I? Why were you so rigid on a consistent check size on Fund I?
  • Why did you decide to expand from being a solo GP fund? What are the challenges and complexities of fund scaling and how did you approach this?
  • What do you think about uncapped notes?
  • Why do you like big boring companies?
  • How did you meet Ryan Graves @ Uber and how did the Uber investment come about? (even more about that here)
  • Where does David still see inefficiencies in the current venture model?


I hope you enjoy it. I had fun doing the interview.

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. It helps you discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded.








Behind the Scenes at Startup Weekend

Startup Weekend might be over, but for those curious about how it all went down, we’re happy to share a behind the scenes look at the event with conference podcaster Clark Buckner. On-site at the Nashville Entrepreneur Center (EC) for the event, Clark spoke with participants, sponsors and mentors to see what they had to say about #SWNash and the Nashville startup community in this series of short interviews. Previously at TechnologyAdvice, Clark continues as a full time podcaster integrating custom content strategies with organizations around the country, Southeast accelerators and digital media marketing conferences. You can also find him at his weekly podcast “The Nashville Entrepreneurship Story” as told by the EC.