Encore - The Venture Capitalist with Heather Redman

Liz Tinkham (00:18):
Hi, this is Liz Tinkham and welcome to Third Act, a podcast about people embracing the third act of their lives with a new sense of purpose and direction. The Third Act begins when your script ends, but your show is just not finished.

Liz Tinkham (00:34):
Today, I’m talking with my good friend, Heather Redman, the venture capitalist. After a successful career as a lawyer, Heather slowed down somewhat, played more tennis, and began thinking she was a bit over the hill. Until one day her teenage daughter asked her what all the other moms really do, and she realized she wasn’t done yet. She came back to work stronger, with more purpose, and with a goal to build our community in Seattle, and to garner more respect for women in tech. Today, Heather is the founder and general partner of Flying Fish Ventures Fund in Seattle. Heather, welcome to, Third Act.

Heather Redman (01:08):
Thank you. What a lovely introduction.

Liz Tinkham (01:10):
Well, it’s all about you. It’s all true. I think teenage daughters are the perfect mirror of their mothers’ insecurities. Mine used to always say to me that she wanted to be a stay at home mom. And of course, this is right during the middle of some huge work crisis, she would tell me that. It sounds like yours was the same in some ways.

Heather Redman (01:29):
Yep.

Liz Tinkham (01:32):
You have a really interesting backstory because you’re a bit of a hippie. So tell us about that.

Heather Redman (01:37):
Yes. I was born in the ’60s in California, and I think for a lot of people who were born in the ’60s, this probably happened to them, too, but maybe my story is not super typical. And I ended up having three parents because I acquired a stepdad along the way, too, who were all super active, anti-war protesters, women’s liberation advocates, anti-racism advocates. I remember being at the home of some of the Black Panthers.

Liz Tinkham (02:12):
Oh my goodness.

Heather Redman (02:13):
Being with Jane Fonda, Alan Ginsburg, all as a little kid. So we lived for a while with Cesar Chavez, so there’re just endless, weird childhood stories of-

Liz Tinkham (02:27):
We’ll do another podcast on that.

Heather Redman (02:29):
Yes. Yes.

Liz Tinkham (02:30):
Heather, Act One. Okay.

Heather Redman (02:31):
Yeah. Yeah. Very unorthodox upbringing in lots of communal situations.

Liz Tinkham (02:36):
Wow. And then, so you ended up at Reed College, which is the academic Nirvana for hippies. What’d you intend to study there?

Heather Redman (02:43):
Yeah, so my parents, when I was about 10, moved to a rural part of Oregon, and so I had to do a lot of conforming when I was in that environment, after having been raised in this free child system. And so Reed was a return back to my early roots. And when I went there, I didn’t really have a specific course of study in mind. I just knew that I wanted to find a way to be financially independent. And Reed’s a pretty traditional curriculum, so it’s physics, chemistry, English, that sort of thing. It’s not for very creative majors. And ultimately I just decided, “I’m going to go to law school so I can do whatever I want,” but just probably important. And so I studied English literature, which of course is lying around reading novels and writing papers about them, which is a great way to go to college.

Liz Tinkham (03:40):
Well, clearly you’re brilliant, you get into all the top law schools. So why did you choose to go to Stanford?

Heather Redman (03:47):
Well, it was funny, because I actually visited Yale and Harvard, and Stanford, because obviously it came down to those three as the logical choices. And then I got a call from an alumni from Stanford, who was doing their recruiting for them, obviously just someone to talk to, but he said, “Hey, you can go to any law school you want and you’ll do great, but would you rather, when you’re studying walkout into the quad and see people playing hacky sack in the sunshine, or freeze your butt off in New Haven or Cambridge?” I’m like, “Yeah, hacky sack.”

Liz Tinkham (04:29):
Fantastic. So how was it, as a girl from the commune going to Stanford?

Heather Redman (04:34):
It was a bit of a shock, and this something I always try to tell people who are from small, rural towns, as I was, you underestimate the capabilities if you don’t get, at an early age, the opportunity to play in the big leagues. So one of the things that really surprised me was how intellectually capable and prepared I was, relative to my peers who had come from all of these universities that I thought were so important, and the people there must be so brilliant. And so it was a great experience in terms of gaining some confidence in my own intellectual abilities by putting myself in no longer a small pond, but a bigger pond.

Liz Tinkham (05:20):
It’s interesting. So how did you overcome that fear? Because I know you really well. You’re very fearless. So I assume it’s all probably always been part of your DNA, but was there something that woke up inside you while you were at Stanford?

Heather Redman (05:33):
Not really. I would say that that’s a little bit what we’re going to talk about later, when we get to my third act. I feel like I actually have been quite fearful and cautious a lot of my life and it wouldn’t show up that way to other people, but I always think you have to measure the what-are-you-doing versus what-could-you-do? Are you living up to your potential? And I would say I’ve sandbagged myself not infrequently in life, and probably even in law school, just not thinking big enough about what I could do, and should do, but just being satisfied, “Oh yeah, I’m doing well. I’m standing up in the lineup of talent here really well,” but not necessarily pushing myself to do everything I could do, more being satisfied if I’m doing well in comparison to others.

Heather Redman (06:31):
One of my big drivers, as a result of my childhood was being financially secure, and standing on my own two feet. And I remember watching a 60 Minutes, this was shortly after I graduated from law school. I remember watching 60 Minutes, and it was this segment on divorced women in Beverly Hills who were living in their cars. And it was basically this idea of women not having financial independence, and ending up on the short end of the stick, having relied on somebody else to earn your money and take care of them. So corporate law and a big law firm really appealed to me in terms of being able to create that career that I thought a woman could have. Because I think we’re all still, in our age group there were certain careers that were semi-open, and other careers that maybe weren’t. And so we were looking for where we could build our financial independence and have a true professional identity. And a large law firm, corporate law, seemed like a possibility for that.

Liz Tinkham (07:34):
Eventually you move in house, but you realize you want to change your identity from being “the lawyer.” Why?

Heather Redman (07:42):
Yeah. So this is something, if you talk to lawyers, I think they universally feel, and I don’t think it’s changing yet, and maybe it will in the future, but what happens in the business world as a lawyer is that you are viewed in a very circumscribed and not very favorable light. You’re viewed as the blocker that you hear people say it’s illegal, and everyone rolls their eyes-

Liz Tinkham (08:10):
That’s going to take forever. Yeah.

Heather Redman (08:12):
Yeah, yeah. And so you’re no value add, you’re just this necessary evil. And so even people who have a ton of other capabilities, if people still identify them as lawyers, they tend to get shoved into that box. And so I was very interested in seeing if I could move over to the business side and shed my lawyer identity and then hopefully have other opportunities opened up to me as a result.

Liz Tinkham (08:39):
And did that work?

Heather Redman (08:41):
Yeah. Yeah. I think that’s why I am where I am today, is I made that important decision, and it’s sad because I think the law is tremendously valuable, and I actually enjoyed being a lawyer quite a bit, but even today, for our firm, I’m not the one who handles the legal work, because it’s dangerous for me to get too far into that box, because I’ll get pulled back in and then I’ll get that label again.

Liz Tinkham (09:05):
Eventually you end up as a principal at Summit Power Group, doing energy projects. So, say more about that company and what kind of job did you have there?

Heather Redman (09:15):
Yeah. That was a great opportunity because the internet had imploded at that point. I’d had a couple of different, great startup rides in internet land, one of them leading into an IPO, great gig. But the energy sector, it’s hard to roll back the tape and remember this, but before Enron exploded and imploded, people viewed energy as this really sexy area. And there was just a lot of money being made, a lot of interest in the area. And so that was the time that I joined Summit, and it was a very small team and they were thinking about wrapping up the business. And then I took the opportunity to say, “I will join you and let’s keep going.” And that led to just really interesting project finance work, but it was a family company, because it was a couple of brothers, and me, and another guy. And so it was a closely held corporation, and very family-oriented. So they were super supportive when we made the next decision, which was, “Let’s get a new family member in our lives,” which was adopting our daughter.

Liz Tinkham (10:26):
So how did things change then, for you, when you adopted your daughter?

Heather Redman (10:32):
Even in anticipation, and this is something, I think, it’s been written about by Sheryl Sandberg and others, but when I decided I was going to get a kid, either biologically or by adoption, I started scaling back my ambitions. And I started feeling that I was pushing my husband more, “You go do,” living vicariously through him, which is of course women did in the fifties and before. But I also felt like I was limiting things right and left, to try to make room for this kid. And maybe that’s smart and sensible, and that’s what we should all do. But for me it felt very wrong, but also very inevitable. So I kept constraining my role at Summit. Several times I was asked to be the CEO and I was like, “No, I can’t do that. I’ve got this kid,” and I kept wanting to have really interesting work, but not take on leadership of more than I had to, so lead things, but I would also always be turning things down.

Liz Tinkham (11:39):
Do you remember, you touched on it a little bit, your identity changing? Did you feel different about yourself?

Heather Redman (11:46):
Yeah, I think I did. And I think I started, my husband talks about how, when I turned 40, I instantly switched my wardrobe to this really dowdy wardrobe compared to my normal wardrobe.

Liz Tinkham (12:00):
Oh my goodness. I can’t imagine you ever being dowdy.

Heather Redman (12:03):
I know, right. And then he said it only lasted for a month and then I switched it back. Thank God. But there’s all this stuff freighted around motherhood. And even though I had step-kids already, it was really a different thing. And there’s a lot of pressure, too, in elementary school settings, to create a social life for your kid, by being part of the full-time mom thing. A lot of women have talked about this, but I definitely did a lot of time pretending to be a stay at home mom, at the same time that I would be working in my Lululemon, in the car, waiting to go in to do the group workout with the other moms.

Liz Tinkham (12:52):
I did the same. I did the same.

Heather Redman (12:54):
It’s a thing.

Liz Tinkham (12:54):
It is. Good and bad, but you shouldn’t have to feel badly about it. So that gets us to the opening story. So your 13-year-old daughter, what does she say to you?

Heather Redman (13:04):
Yeah, this is a hard thing in many ways, because I don’t like to throw shade on other women’s choices, but my daughter, in her very progressive, all-girls school, I think was talking a lot about empowerment of women and women’s role in society. And she started really noticing the mothers of her friends, and noticing my friends, also, my female friends and she knew I had a job and she says, “I spent all my life under your desk, Mom, because you were always working,” which of course I’m like, “No, I was dogging it when you were little, you don’t know what I was sacrificing for you.” But she started saying, she would ask, “What does so-and-so do?” and I would say, “Well, she used to,” and I would talk about her career 10 years ago. And then my daughter would say, “Well, what does she do now? Because when I go to their house, she’s not doing anything, and she bugs her kids and she doesn’t seem happy.” She was watching things and-

Liz Tinkham (14:14):
The mirror. Very observational, right?

Heather Redman (14:17):
Yeah. Yeah. Seeing things with a fresh eye. And I realized, and some of her friends, you were saying about your daughter saying she wanted to be a stay at home mom, but some of her friends, she would actually say, “My friend so-and-so says she’s planning on quitting her job as soon as she graduates from college and has a kid. And she just wants to live like her mom does, which is pretty high on the hog, without earning any money.” And this whole thing just freaked me out. And so I started formulating a plan of, “Well, what should I do next?” What should I really do, to both do my part for society and give back, because I’ve had so much privilege, but also really provide a good role model to my daughter and to other women, or why, at age whatever I was then, I guess, or mid-forties or something, that you’re not done. Just because you have the financial security to be done, doesn’t mean you’re done.

Liz Tinkham (15:20):
Yeah, the vocational freedom. Right. So voila, you wake up, you say to Rick, “I’m back.” And I don’t know if you guys are reading this great book, which I’ve talked about many times already in this podcast. It’s called Younger Next Year, which is one of my favorite books, except for the chapter on divorcing the first wife. Which is in the men’s version-

Heather Redman (15:40):
I’ve repressed that.

Liz Tinkham (15:41):
I know. It’s just so upsetting that they put that in the men’s version, but anyway, it plays a part. So, talk about that. When you’re thinking about coming back, how did you think about that?

Heather Redman (15:52):
Yeah, I really thought about Younger Next Year, in terms of all the nutrition and exercise advice that gives, but really that was not the part that really hit me. The part that hit me was the community part, because I am an only child. As you know, given my background, I lived all over the place and had crazy uprootings now and again. I’m also an introvert, so being with other people doesn’t necessarily come naturally to me, and this idea of really being connected and really participating in a community, as however you want to construct that, was very impactful. That was the part of the book, which I think is the last third that I was like, “Oh, holy crap. This is the stuff I’m not doing that I need to start doing.

Liz Tinkham (16:40):
Yeah. It makes a very strong case for diet or exercise, exercise, exercise, and community, but particularly for men, who lose it. So you double down your efforts to build up the Seattle community. You go back, you get your job at Index. You’ve done, and I’ve met you through this, I’ve met you through so much of the community, and tell us about what you’ve done. Because I think it’s exemplary, and as other listeners think about, “Well, I want to get more involved in the community,” what’s your example?

Heather Redman (17:15):
Yeah. I think, to me, first of all, it’s being open to a lot of people and being open to helping out. Even this morning, I had a call with a great CFO of one of our major local companies in Seattle, who’s a woman, and I’d never met her before, but it is creating new connections that way, and new connections with people who are going to be similarly minded to you about their responsibility to the community. And so it’s not only about you, and what you can do, but also helping with other people to create ideas about what should be done, and then getting behind those ideas.

Heather Redman (17:56):
But for me, one of the ways to do that was really to get pretty involved in local politics, as well as, obviously, our own corner of the national political spectrum. We’re lucky that we have a lot of really cool politicians in Washington State, some of whom are amazing women, by the way, like our two senators, and our former governor, and other folks that can think of. So I started being pretty active in political campaigns, locally, everyone likes to get involved in the big presidential stuff, but I think it’s much more interesting to be involved locally.

Heather Redman (18:33):
Then that led to being involved with a lot of business organizations, who also were involved with politics, because you have to be. It’s always nonprofit, business, and government that’s going to move society forward in tandem, hopefully. So to me, really getting in there and trying to help and shape that was the key, but I also spend a lot of time getting to know the big restauranteurs in the region, getting to know the people that run the art museum, getting to know people that run nightlife. Just trying to figure out, who are the people that are really causing things to happen in our region, and then how do you provide benefit to them by them knowing you, and vice versa, and just being that connector?

Liz Tinkham (19:25):
Part two, though, the comeback. So part one is community, part two is to get more women respected in tech. I know you’re really passionate about that. So how are you going about doing that and what do you see?

Heather Redman (19:38):
The thing I have tried to encapsulate this in, when I try to encourage other people to think this way is, what’s your highest and best use? And so, when you have vocational choice, which I love how you put that, it’s getting to think about, well, what would be very challenging for me? So, how can I feel like I’m having that midlife crisis and having it be a constructive process? A lot of people want to run ultra marathons, so what’s my ultra marathon equivalent? And then, what’s something that only a few people who happen to have my characteristics could actually do?

Heather Redman (20:18):
So, as I looked around and looked at my two drivers, one of which was to help the region, and the other of which was to really help the status of women, broadly, I thought, this venture capital tech thing is the bullseye for what’s going to be challenging for me, and also beneficial to those two causes, and is something that only a few people I think can pull off, and that I was situated to pull off. And that’s really because I believed that power and money are so tightly linked. I believe that tech is the key to money, in this next era that we’re in. And so when you think about that, you think about, “Well, where is the real power position in money related to tech, and it’s clearly venture capital.” And, no surprise, that is a place where women are really, really poorly represented as well as BIPOC folks as well. It’s a very white male world, and white male Ivy League world too, for that matter. It’s a very small sliver of society.

Heather Redman (21:31):
So I thought, well, being a founder of a venture firm, when I started this, and now there are more, but they’re still all in that, “Can I make this work?” stage, but when I started, there were probably maybe a few dozen women who had actually started venture funds, out of thousands and thousands of funds. And to be an owner of a venture fund and to be the founder and to be, in my case, the face of the firm, it’s very unusual. So it is my ultra marathon, for sure, and it’s every bit as hard as an ultra marathon. But when I need to get motivated to go spend another day, not in the sun, but on Zoom calls all day, it’s probably because I do believe this makes a big difference.

Liz Tinkham (22:18):
Are you enjoying it?

Heather Redman (22:20):
Oh yeah. It’s a great job. And I actually like the parts that a lot of people don’t like, I like the money raising part because it’s all about telling a story, and it’s also very binary, either they want to give you money or they don’t, so it’s very easy to tell if you’re being successful.

Liz Tinkham (22:39):
It’s like being a waitress, you either get a tip or you don’t, right? I used to love being a waitress for that reason.

Heather Redman (22:44):
I liked being a waitress, too, actually. I thought that was fun.

Liz Tinkham (22:47):
I did too.

Heather Redman (22:48):
Yeah. But the part of working with founders and CEOs, and getting to hear new ideas and getting to, because we invest so early stage, I also get to influence those ideas. It’s not just about writing the check, it’s also about saying, “Well, have you thought about this?” And, “What if you went after this market, instead of that market?” Or, “What if you put more emphasis on this part of the tech versus that?” So it’s a super creative, but also good multi-tasker job to have, because you have a million tasks and your job is never done. So you need to be able to move very fluidly from one thing to the next, and you need to be happy with, “Well, I sort of finished that, but I’m not really done, but I can’t be.”

Liz Tinkham (23:34):
So now you’re in a position of power, in the sense of, you own the money as the funder, how is that, being a woman, in terms of raising the fund as well as talking with entrepreneurs?

Heather Redman (23:47):
Yeah, it’s interesting. I think it’s pretty good. I think that the biggest impact that I have is actually on male teams that come in and pitch us. Everyone always expects, to be a woman in this position, that you’re going to have this great impact on women-led teams. But first, there were still very few of them, and they are very happy to see you there, and you’re very happy to see them there. But I think the bigger impact is on all-male teams, who have never had to ask a woman for something who’s been in this much power over them. And so that to watch their minds remodel and their pattern recognition shift as to who could be in that position, and who is going to be the decider of my fate in terms of getting money, that’s really, really valuable.

Heather Redman (24:39):
And it does make you feel like you’re making a difference daily, and hopefully, a lot of these teams are very young, and so hopefully they’ve had experience with women in power. But in tech, there’s still not a lot of that. And so we need to really work on that area of representation. Ditto with BIPOC folks as well, having to ask a black man or a black woman for money, for your Ivy league, white founder, would be a different experience, and one that would be very beneficial.

Liz Tinkham (25:11):
We probably have listeners who are thinking about doing the same thing, and any advice, in terms of being a venture capitalist, starting your own fund, any advice there?

Heather Redman (25:24):
Yeah. Yeah. Unfortunately, it’s something that is hard to do unless you already have a lot of financial security, because it is a very long time until you can possibly think that you are in the same place that you would be if you just took a job.

Liz Tinkham (25:39):
Yeah. You basically don’t get paid for a while, correct?

Heather Redman (25:42):
Yeah, you don’t get paid for a long time. And even from a subsistence standpoint, you’re waiting a long time until you really get to catch up. It’s a 10 year journey before you get to catch up with all the money that you could have earned running a company, or being in the C-suite or whatever. And then you have to, I think, enjoy raising money. So you have to really believe in your story, and you have to be in sales enough to know that you’re going to hear a lot of, “No,” and that’s okay. But that’s just part of the gig. A lot of people are like, “Yeah, I would love to work with young companies, and help them and mentor them,” but yes, that is a very big part of the job, and it is the fun part of the job, but the raising of the capital is, and especially for a new fund, is probably even more important.

Liz Tinkham (26:32):
Mm-hmm (affirmative). Yeah, you have to be fearless in that sense.

Heather Redman (26:35):
Yeah.

Liz Tinkham (26:40):
This podcast is sponsored through the Athena Alliance, which is, we get senior women onto boards, that you and I are both the pioneer members of the Athena Alliance, because we’re on boards. And Athena does a great job of preparing women for board service, as well as for more senior jobs. But you always say to me, and I always tell other people, “Women should become CEOs first.” You know this. So what’s the takeaway for listeners?

Heather Redman (27:05):
Yeah. I always ask people to do a couple of thought experiments. So first of all, I always ask women to do a thought experiment that somebody told me to do, and it shook me to my core. And that thought experiment was, imagine that you are your twin brother. And so imagine you have every characteristic that you have now, but expressed in a male form, where would you be now, in your career?

Liz Tinkham (27:30):
Oh, that’s a horrifying thought.

Heather Redman (27:32):
I know. Right?

Liz Tinkham (27:33):
Yeah. That’s interesting.

Heather Redman (27:35):
Very horrifying thought.

Liz Tinkham (27:35):
Wow. I never thought about that.

Heather Redman (27:36):
Right. And from that thought you will quickly conclude, “Oh yeah, I wouldn’t be going onto boards at this point, I would be running some gigantic company.” And so that’s what I ask women to think about doing, is again, I had this epiphany in a Women on Boards group, where there were probably 30 women in the room and some of them were already on boards. Some of them were getting on boards, but all of them had stopped their ascent. They were no longer thinking about CEO. They were CFOs, they were CMOs, they were whatever they were. And they were basically going to keep doing that job, and maybe even do it again for another company, but they weren’t really trying to be CEO. But they were starting to think about being on boards, and when they got on enough boards, they were probably going to stop their day job.

Heather Redman (28:26):
And I stood up in this group, and I said, “I think you guys need to look around. If you were all men, you would not be in this room right now. You would still be saying, “Yeah, I’m interested in boards, but later, because I haven’t been a CEO yet.””

Liz Tinkham (28:40):
Wow. Wow. Yeah. You’re very right. You’re absolutely right. And that’s a great way to think about it, as your twin, your male twin.

Heather Redman (28:49):
Oh my gosh. It’s phenomenal. You have sons, so you can probably see yourself reincarnated in that form right now.

Liz Tinkham (28:58):
I sure can. Yeah. And I’m like, “Wow you’re so fearless.” Yeah, exactly. So, that’s a great lesson.

Liz Tinkham (29:05):
I always close my podcast by asking guests what they’re not done with yet. We might require a podcast or two more for you. For you, because Jenny Durkan’s seat, our Seattle mayor, is vacant. So I don’t know. Is that your next act, or what else do you have in mind?

Heather Redman (29:22):
It’s so funny. People always ask me if I’ll run for something, or something else and of course, I think everybody would be happy to be appointed to run something, but I don’t think even I would be happy to be appointed Seattle Mayor right now.

Liz Tinkham (29:35):
So difficult.

Heather Redman (29:36):
Nobody wants that job. Yeah. Definitely not politics. I do regret not being a CEO, but I think, now wearing my venture hat, I am in that position, and that was not a position I plan to relinquish for any other position, but that position will hopefully help me encourage and facilitate a lot of other women and BIPOC people becoming CEOs. Because I think that’s the job that all of us should be working on right now.

Liz Tinkham (30:06):
Yeah, absolutely. Well, you are such an inspiration always to me, for getting going and doing good. Thanks so much for joining me on this episode of Third Act. Where can we find you online? And we’ll put it all in the show notes.

Heather Redman (30:18):
Yeah. So @HeatherRedman, for Twitter, and I’m also pretty active on LinkedIn and just Heather Redman on LinkedIn.

Liz Tinkham (30:27):
Great. We’ll put that in. Well, thanks so much, Heather.

Heather Redman (30:30):
Thank you. This was wonderful to talk to you, Liz, and thank you so much for everything you’re doing.

Liz Tinkham (30:36):
Thanks for joining me today to listen to the Third Act Podcast. You can find show notes, guest bios, and more at thirdactpodcast.com. If you enjoyed our show today, please subscribe and write a review on your favorite podcast platform. I’m your host, Liz Tinkham, I’ll be back next week with another guest who’s found new meaning and fulfillment in the third act of their life.