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Episode 35: From intra to entre: Insights from a VC boss lady

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Sippin' & Shippin'
Episode 35: From intra to entre: Insights from a VC boss lady

Tanya Phipps|March 17th, 2023

As we continue our month-long WHM series, the Sippin’ & Shippin’ crew chats it up with friend and tech legend Maia Benson, venture capitalist with Forum Ventures. She shares her story of how she got started in the tech industry, her transition from intrapreneur to entrepreneur, and where she is today. We hear her thoughts on the power of mentorship and the impact it’s had in her career. Plus, she drops some tea on the current trends and changes happening in the VC world.


2:27 Maia’s background 

4:34 Her journey into tech and intrapreneurship

6:42 Move fast and learn

9:47 Cultivating an entrepreneurship mindset into traditional corporate culture

11:33 Intentional mentoring

14:10 Honing in on talent and ensuring a diverse hiring pool

17:45 Confidence is gained and built from an early age

21:01 VC market trends and changes

24:57 Finding opportunities, even in an economic downturn

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Brian Weinstein: Welcome, everybody, to Sippin’ & Shippin’. I’m your host, Brian Weinstein. We’ll be kicking it here every other Friday, quenching your thirst for an insider’s take to enhance your customer experience. So grab your drink of choice, kick back, it’s Sippin’ & Shippin’ time.

All right. Welcome, everybody, to another episode of Sippin’ & Shippin’. I am your host, Brian Weinstein. And with me again this particular Friday, Caitlin Postel.

Caitlin Postel: Hey, Brian. Back again. Happy to have you back. I know you gave me the opportunity last week to take over. We had a lot of fun, but looking forward to this episode today.

Brian Weinstein: You know what? I have to tell you, and for those of you, hopefully all tuned in last week, we had the first of our month celebration of Women’s History Month. Caitlin hijacked the show last week. It was just fantastic. You guys did a tremendous job obviously. And I texted all of you this, very proud to get to work with some really strong female leaders. It was really nice to hear some of the backstories.

Caitlin Postel: Yeah, very interesting. We had an almost doctor, we had Hannah Montana, and we had Sandra Dee. All turned out to be logistical leaders and ladies that I’m, I’ll echo that sentiment, very proud to work alongside of and learn from every day. For sure.

Brian Weinstein: Yeah, absolutely, absolutely. In terms of female leaders, Women’s History Month, an absolute rock star we have with us today is Maia Benson. Maia, how are you?

Maia Benson: Hi, Brian. Hi, Caitlin.

Caitlin Postel: Hey, Maia.

Maia Benson: I’m so happy to be here. What are you guys sipping on our podcast today?

Caitlin Postel: Bringing it back to the sipping topic. All right. You put me on the spot. I have nothing more than some H2O here, staying hydrated.

Maia Benson: That’s awesome. Brian?

Brian Weinstein: Me too. Me too.

Maia Benson: Yeah, same here.

Brian Weinstein: I’ve got my big jug of water, taking it easy today. I may have overindulged a little bit last night. Just saying.

Caitlin Postel: There it is.

Brian Weinstein: Just trying to keep myself hydrated.

Maia Benson: In many countries, they call Thursday, Small Friday. So good for you.

Brian Weinstein: Right, exactly.

Maia Benson: I’ve got some Seagram’s, guys. It’s not what you think. It’s ginger ale.

Brian Weinstein: Oh.

Maia Benson: I brought Seagram’s to the party. [inaudible 00:02:21]

Caitlin Postel: Different kind of bubbly.

Maia Benson: Not quite 5:00 yet.

Brian Weinstein: Exactly, exactly. So Maia, for those out there, and I’m sure there’s very few of them, who don’t know you, could you just give us a little bit of background on you, and where you came from, and a little bit of your history?

Maia Benson: I’m a native Midwestern gal, grew up a lot in Chicago. Grew up out in the valley, really as a product manager building SaaS products for really non-SaaS native companies. Grew from product management into general management, so running portfolios of products. Really throughout that process in big corporate America, was the intrapreneur. All of that product base, and laddered up into portfolio base, was net new stuff to the big corporate players. That was the early chapter. As I thought about that experience, what became clear to me is, it’s such a luxury in big corporate when you have built in distribution, built in resources.

Brian Weinstein: Yep.

Maia Benson: Those are really, really critical and important leavers to have when you build and launch new stuff. But the flip side is, there’s a lot of navigation to transforming firms into the digital, data, A/B test, take some risk, kind of yeses are good, nos are equally as good, let’s just move fast and learn.

Brian Weinstein: Yep.

Maia Benson: So what I was looking for, as I was building stuff for big corporate, was an environment where those baselines were already really well established.

Brian Weinstein: Yep.

Maia Benson: So after big corporate, I jumped to a growth company called Shopify, second US employee. They were brand new to the shipping space.

Brian Weinstein: Okay.

Maia Benson: So I came in, and built and ran everything outside of R&D. Had an absolute blast working in a culture where some of those first principles that I just outlined, digital native, data native, hypothesis based, test oriented, risk oriented, were all there and true.

Brian Weinstein: Just a question, just to dial back a second. What drove you towards tech?

Maia Benson: It’s such a great question. It’s such a great question. If I’m very, very honest, I think I, post undergrad, landed in San Francisco.

Brian Weinstein: Okay.

Maia Benson: Didn’t know what I wanted to be when I grew up, like many recent grads. The best advice I had was from my dad who said, Totally okay you don’t know what you want to be when you grow up. Go get some great training. So I was very fortunate to have a first job at Xerox at that point in time, which had a world-class, really consultative based selling motion, value-based selling motion. So got some good foundational training. And I got lucky, Brian, and that it was the mid-90s, and Xerox was going through, real time, the analog to digital transformation.

Brian Weinstein: Okay.

Maia Benson: As a salesperson at that point in time, I was really selling some of the earliest and first digital copiers and fax machines to the market. So that’s the answer and the anchor, and it’s candidly nothing more than sheer luck in terms of the analog to digital timing transformation.

Brian Weinstein: Interesting. Okay. I never really thought of Xerox in that role, and having such a big transformation. But I guess when you think it through…

Maia Benson: Remember, Xerox is world-class R&D famous. They had the PARC Research Center, the Palo Alto Research Center. And really, if you’ve read the story about, I think it was Bill Gates walked through or Jobs walked… It was Jobs who walked through PARC, got a tour and saw the mouse. So the [inaudible 00:06:24] really fundamental early days tech. Remember guys, this is the mid-90s.

Brian Weinstein: Yeah.

Caitlin Postel: Yeah.

Maia Benson: Was born out of Xerox. So to your point, Brian, most people wouldn’t think about that. It’s not something that somebody’s going to think about during the day, but just providing added color and context.

Caitlin Postel: Yeah. Talk about timing is everything. I was taken aback by that answer, but what better place to start with tech than with the fax machine and the copy machine?

Brian Weinstein: And the copy machine.

Caitlin Postel: And the copy machine, which is wild. But you said something interesting that really perked my ears up. And that was, move fast and learn. I guess I want to talk a little bit about that. What better way to move fast and learn than being the second employee at Shopify? What can you say about that intrapreneurial spirit, being a woman, being the second employee, and really getting things going at Shopify? What was that like?

Maia Benson: That was their native DNA. I joined a current in a river that was flowing that direction rapidly. Period. Hard stop. I will say I was fortunate, in building new stuff for big corporate, to have the umbrella executive support to also do that in those areas, which you have to have or else I wouldn’t have been successful with any of the internal builds and growth. That is a first principle when you’re living in a digital-only, highly disposable, highly easy and cheap to test world. So was just thrilled to join a company where, like I said, that was the main current, and the expected way of building. I wouldn’t say I brought anything net new to that river. I brought some product brief inputs, and how to really make sure we were building products, and had really clear definition of the market segments we were building them for, how big those market segments were, what the other competitive or substitutes were. Those were some value adds on the product side.

But fortunately, and core to Shopify success, is their absolutely DNA native, A/B/C/D test. Yes, those are good. Data trumps everything. Learn, ship it, launch it, get it live, and then continue to collect feedback, and keep doing the same cycle, rinse and repeat.

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Brian Weinstein: When you jump into that current, you have to be a strong and fast swimmer though.

Maia Benson: Yeah.

Brian Weinstein: So clearly you’re able to do that.

Maia Benson: Absolutely. When I joined, there were probably 12 of us building all things shipping.

Brian Weinstein: Right.

Maia Benson: What’s also great, to your point, Brian, is we were all fast swimmers, but we were small when we first started. And because of that, we could even swim faster. We built a culture of really deep interconnectedness. Many of those original folks scaled with us all the way through ’21, even as 5Xed as a team. So yeah. You’re right. You got to be a fast swimmer. And if you’re lucky, you’re on a team of other fast swimmers that are hyper connected. Because when you’re hyper connected, and you have those fast feedback loops and communication loops, you can swim even faster.

Brian Weinstein: Yeah. It’s funny too, on that note, with companies getting bigger, I feel like there’s a push right now, with bigger companies to really focus on, Hey. How do we get back to being nimble? How do we stay nimble? Because the development and the intrapreneurialism is integral to a company not stagnating. So having the right people in place that can defy the big business and push an entrepreneurialism within is critical.

Maia Benson: I couldn’t agree more. To me, great CEOs of big public companies fundamentally understand they’re going to have different businesses at different points in their growth and their life cycle that require different sets of talent. So if you’ve got a cash cow that’s mature, you’re operating. You’re maximizing for yield on that investment. And that’s fine. That’s a set of talent. If you’ve got a growth part of your portfolio, then absolutely, Brian, you’re going to need some inflection points and some leadership in there, in terms of folks that can lead with a little more nimbleness, and an innovative process and culture orientation. Then hopefully, you’ve also got a few baby birds, as I would call them, experiments.

Brian Weinstein: Yep.

Maia Benson: So this is called portfolio management. Harvard, years ago, did a great article on a framework called H1, H2 and H3, Horizon based portfolio management, that I think is a great framework that never ages, in terms of how to do that well at scale.

Brian Weinstein: Yeah.

Let’s take a step back in your career journey. This is really with this focus that we have this month with Women’s History Month. Can you tell us a little bit about… Obviously, in tech, it’s a lower percentage of women to begin with. Did you have particular mentors, whether they were other women or men, that really helped you along the way?

Maia Benson: Absolutely. Both. Period. Hard stop. That’s the simple answer. I don’t think any of us grow without critical mentors. I was incredibly fortunate to have some great female and male mentors along the way. I will say, there’s a lot of great attributes that I think about when I think about the mentors that influenced me. But one thing that really rises to the top is, I used to have male executives pull me into meetings and purposefully ask me one question around the table so my voice could be heard. So there was deep intentionality, not only of coaching behind the scenes, but giving me the opportunity where the decisions were made, to have an intelligent point of view. And of course, before going into that, having that mature intelligent point of view; socialized with mentorship and others. So I encourage more leaders throughout the growth of your career, really at any stage you’re in manager and up, to be a mentor, share what you’ve learned, help grow people. It’s incredibly rewarding.

And then as you grow into the C-suite, obviously continue to do that, but also support institutionalized programs and matchmaking to make sure you have a culture of growing and nurturing that talent. It is incredibly expensive to bring in new talent to an organization. The onboarding, all that is required to indoctrinate someone into the culture and into their role to drive outcomes is expensive. So I think it’s very cost-effective to hire really, really well upfront, and systematize.

Brian Weinstein: Mm-hmm.

Maia Benson: That’s big Friday word here.

Caitlin Postel: Yeah.

Maia Benson: I need another shot of Seagrams here guys. Systematized kind of, that mentor mentality.

Brian Weinstein: Yeah.

Caitlin Postel: Yeah. It’s so refreshing to hear that that was your experience.

And Brian kind of touched on it before about, and you alluded to it as well, having the right people in the right seats. So as you began to advance in your career and leading large teams, what did you do as a leader to ensure diversification of hiring, making sure you had those right folks and really honing in on that talent to be able to build your teams?

Maia Benson: It’s a mass quantification. Set conscious goals around ensuring diversity in your hiring slate. So I’m not making a hire for this open opportunity unless I see two candidates in a pool of five at least that are not mainstream, for lack of a better word.

Brian Weinstein: Yeah.

Maia Benson: So you have to consciously quantify the inbound to ensure diversities in the hopper. And then consciously work, as I mentioned before, once you’re bringing talent in whoever ends up in the company hopper, that you’re engaging diversity thoughtfully and supporting growth for the talent you have.

Brian Weinstein: Sure.

Maia Benson: So you’ve got to work the external quantifiable goals with diverse hiring slates. And then once they’re in, you’ve got to keep them and grow them.

Brian Weinstein: Makes sense.

Maia Benson: So those are ways. I think all companies should have targets. I think you should have KPIs and ideally targets, but I think the nuance is for whatever role or function, those targets may be different. So if there’s a reflection in the market where in customer service you can get to 50/50 or better on diversity, great. If you’re realistically living in logistics engineering land, if you have a tech funnel and then you have a logistics funnel on top of that, the market doesn’t look like that in terms of diversity available. So be thoughtful, be mindful, quantify; but we have to also acknowledge that the supply is not equal in all types of roles.

Brian Weinstein: Yeah. It’s funny you say that because it’s so important to do it, but you have to be realistic to your particular market. I mean when you start to think back on the percentage of women in tech 20 years ago, if you said we’re going to go out there and try to go 50/50, well you wouldn’t be able to find enough candidates to get to a 50/50 number back then.

Maia Benson: Yeah. By the way, it’s declined since back in the day, like the seventies. We’re going the wrong way.

Brian Weinstein: Right.

Maia Benson: But you’re absolutely right Brian. And on top of that, so those are the easy answers. I think the harder answers is there needs to be more investment in nurturing and making careers in the underrepresented functions more accessible to girls and women as they’re coming up. Just by democratizing and making these jobs really like, Oh, that’s what somebody does? Really, really accept accessible and well understood is revolutionary.

Brian Weinstein: Yeah.

Maia Benson: Because all of us build up perceptions of what something is that could be big and scary, and in reality we all know that’s just not true. So I think it’s incumbent upon all of us to nurture the up and comers as well.

Brian Weinstein: It’s interesting, there’s just so much development that I think happens, especially the differences between men and women from a social perspective. I go back to when I was coming out of college, my wife and her friends, they all talked about they were never pushed to play sports, for example, when they were growing up. And each one of them talked about how when they got into the workforce, now we’re in our mid-twenties when we’re having this conversation, but they were saying when they got into the workforce, they felt behind a lot of their male counterparts because they didn’t have that team interaction. They didn’t understand what it was like to function in that type of world. I literally pushed my daughter, probably kicking and screaming into sports, when she was seven or eight years old. And then she found the enjoyment in it and ran with it through high school playing two sports.

But it’s become so much more popular amongst girls in the US. And I’m proud to see what’s happened is that has made for leaders. Because one thing that you mentioned Maia, and Eva mentioned it on the last episode, was this fear of being in the room that maybe you didn’t belong and that you needed to have your voice, which really speaks to confidence and not being forced into uncomfortable situations. And as a male, I never thought about that. As I grew up, I played sports, I was active, you’re competitive, but you’re working together on a common goal. I never thought about it that way. So the education process and hearing those stories to me was very, very powerful.

Maia Benson: It’s such a meaningful and deeply resonant story with me as well, Brian. So I’m the oldest of four children. I have three younger brothers, and so really the default DNA in the house was a lot of sports. So like you, I grew up playing a ton of sports. And what’s beautiful about sports is not only the collaboration and the team orientation that you’re talking about if you’re playing team sports, but even if you’re not, you’re always testing and learning. You’re always succeeding and failing, real time. I made the shot, I didn’t make the shot. I made the pass, I didn’t make that pass. And so that tolerance for risk and failure can be higher. And so the confidence, the skill set of test and learn and fail and succeed, all of that can come outside of sports too. There are other amazing things boys and girls can do to get those skill sets. But that is what is just incredibly valuable when you have a highly confident person that’s deeply curious and okay to learning, and in an environment that supports success and failure, that’s a recipe for magic and success.

Brian Weinstein: Yeah, absolutely. No, I agree with you a hundred percent.

So shifting gears and speaking of success and failure, we may be in the middle of economic headwinds and things. I know you have Forum Ventures, which is a VC company. So we wanted to get your take on where we are right now, what you’re seeing, the economy, what VC money might be doing while all this is going on.

Maia Benson: I mean we’re talking today on Friday, March 10th, as Silicon Valley Bank is imploding. Literally before I walked into this podcast with you, Brian and Caitlin, I think I just read the FDIC took over SVB. So unbelievable times. Unbelievable, timely question. Look, high interest rates right now. We have a really fun separate podcast with a bunch of smart people to talk about the root causes there. I think the underlying macro drivers are absolutely fascinating. And candidly, I’m not sure if the interest rate hikes are going to ultimately solve our problem.

Brian Weinstein: Right.

Maia Benson: But we’ve got these high interest rates, and Brian, Caitlin, you guys are investors, you put your money somewhere. And so if you can drive a lot of yield from really simple investment vehicles right now that have a lot of yield because of these high interest rates, that means by definition investing in anything else like risky new companies has got to just meet a higher bar of value.

Brian Weinstein: Right. Okay.

Maia Benson: So high interest rates, we’ve seen significantly impact series A, B, C, D and up companies the most. In my world, we’re preceding seed, so kind of really first check inland. We have seen some of that impact in terms of valuation calibration, a little bit more insulated. But excitingly what we’re seeing is because of all of that and higher bars to success, quality of founders is going up. It’s so exciting.

Also, as you guys know, there’s been some layoffs in the tech industry and we are seeing really some of those folks decide it’s a great time during these hectic macro and candidly economic geopolitical wins to put your head down and build. So quality of founders is going up, valuations A and above are coming down. All of this risk becomes very unpredictable for all of us, which even makes the barriers and the risk spin the flywheel in that negative direction.

So from my point of view in the pre-seed seed seat, it’s never been a better time to buckle down and build. Higher quality founders know this is a time now of, I got to build need to have [inaudible 00:23:51] solutions. We’re out of the nice to have days. So I find it incredibly exciting to join at this point in time in this market, like you said, but those are some ways I think about it, Brian. Deals are taking longer, there’s more diligence going on, there’s a lot more dating going on, some other things that are happening, because of the macro world I just painted.

Caitlin Postel: Yeah, I think you said on our intro call, build shit people need to have within a budget. And I love that. Just bill shit people need within a budget. It’s so simple, but I’m sure it’s something that you’re seeing, especially with this higher degree of entrepreneurs.

Maia Benson: Yeah, yeah. We’re back to days of milestone based investing. So build shit that people need, that people can afford to pay for, and ask for investment based on trip [inaudible 00:24:44] and milestones as you build, right?

Brian Weinstein: Yeah.

Maia Benson: So you’re not raising for two years anymore, you’re raising for the next product build that’s going to unlock more traction, more user adoption.

Brian Weinstein: Yeah. Yeah. I went to a great conference this week actually in Manhattan called the Lead, and they had their foremost fifties. It was a lot of entrepreneurials. It’s sort of like their little academy awards for top rising e-commerce brands. One of the round table discussions talked specifically about, when you mentioned the layoffs, they looked at the layoffs as a tremendous opportunity because there’s so much talent then that hits the street again. The personnel that they picked up that they may not have taken but had no choice to, they needed to fill a seat, they can now weed those out and get in quality people who really want and can make an impact to their company and make them leaner and meaner, if you will.

Maia Benson: There’s such a healthy outcome of economic downturns because it does kind of fountain out talent, if you will, which redistributes it. So the market doesn’t win if all the talents condensed around fangs and then a few others. That’s not how markets win. That’s how companies win.

Brian Weinstein: Yeah.

Maia Benson: That’s not how markets win. And we could all candidly argue that’s not how democracies win. So the more we can redistribute talent, not only broadly across multiple companies, but candidly across geographies, I think the better that is for our country here.

Brian Weinstein: Yeah, yeah.

I will say another thing that I saw, which was interesting, and I know I spoke to the people that ran the conference, and this wasn’t intentional, but half of that list of these rising e-commerce brands, roughly half were female founded, which is also fantastic.

Maia Benson: What a fantastic stat. That just kind of made my Friday, Brian.

Brian Weinstein: Yeah.

Maia Benson: I love it. The more and more of the pipeline of those that can lead and drive growth diversifies, the more change we’ll actually be able to realize. When women in context, as one example of folks that are currently not equal, and all others become leaders and have power, then they can really materially affect change. So the more of that we continue to see Brian, the more exciting it is.

Brian Weinstein: Absolutely.

Maia, this has been fantastic. I really appreciate you coming on, giving everybody some background on you, your journey. Also, a little insight into the market, which was great. So thank you very much for coming on.

Maia Benson: Thank you for having me, Brian and Caitlin. I’m raising my Seagram’s virtually to you. Cheers, hang on some water. So happy to be here with you guys today, and going to wish you an awesome upcoming weekend.

Brian Weinstein: You as well. All right, Caitlin, you want to walk us out?

Caitlin Postel: Sure. Yeah. Thank you so much, Maia. Thank you everyone for tuning in. Check us out every other week on your favorite podcast platform. Have a great weekend everybody. Thanks, guys.

Brian Weinstein: Thank you.

Maia Benson: Thank you.

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