Embedded - 185: Nice Mahogany Table

Episode Date: January 25, 2017

Debby Meredith (@DebbyMe) stops by to tell us what it is like being a venture partner and interim VP of engineering. Debby is a venture partner at Icon Ventures. Her website is DebbyMeredith.com. She was on a new podcast: Women Who Code Radio. Computer History Museum's new exhibit is Make Software: Change the World. It opens on January 28, 2017.  After recording, Debby mentioned a book she likes: Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist. January 28th Hats and Hacks Party RSVP

Hello, and welcome to Embedded. I am Elysia White, here with Christopher White. Our guest this week has many titles, VP of Engineering, Software Executive, Advisor, Board Member, and Venture Partner. I'm looking forward to speaking with Debbie Meredith. But real quick, before we get to talking to Debbie, I need to remind you we're having a Hats and Hacks party on Saturday, and I'm not going to say which Saturday, because if it isn't this Saturday, it's already passed.

Okay, it's January 28th. If you haven't RSVP'd, you are running out of time, and I need to order food. Check the show notes for a link with details and everybody who can't make it, we'll send you a few pictures. Hi, Debbie. It's great to talk to you today. Hey, Chris. Hey, Alicia. Could you tell us a bit about yourself? Oh, my. Well, as you say, I have many titles. And I think that kind of represents, you know, the lifestyle that I have constructed, right? I do little of many things and it, you know, keeps me on my toes, keeps me from being bored, keeps me active, and hopefully allows me to add a fair amount of value in a few places that are important to me. Cool. Well, I think we want to know a lot more detail about actual what you do, especially that venture partner thing that sounds so mysterious

to us engineers. But before we get there, let us go to lightning round where we ask you short questions. We want you to give us short answers. And if we are behaving ourselves, we won't ask you for like why and how and all of that. Okay. Should we bring back the dinosaurs? Probably the last time this question will be asked. Oh, that's, no, no. Dogs or cats? Dogs. introvert or extrovert extrovert

any new year's resolutions oh you know the classic to be fitter best way for a co-worker to reach you text email phone call instant messenger is there anything else that's been invented since this card was made? Telepathy. Telepathy. I would say text. My phone is always with me. What science fiction technology or concept do you think will be real in your lifetime? Oh, certainly the virtual reality, the self-driving cars.

I'm looking forward to that so that when I'm older, I'm not dangerous on the road and I can go anywhere that I want. 4 p.m. drink. Ooh, glass of oaky chardonnay. Do you have a tip or trick you think everyone should know? Gosh, I don't think so, honestly. That one stumped me. That's fine.

Well, you know, I always treat other people the way you want to be treated. And, you know, it doesn't cost anything to be gracious. All right. That works. So this one, a longer answer. What is a typical workday like for you? Well, it depends which hat I'm wearing. I could do a typical week. Okay, sure. So Mondays, I am at Icon Ventures since I am a venture partner and that is when we have our partners meeting. So that's typically my Monday.

And it's a meeting that runs most of the day. It's very efficient and well run, but we look at new deals, talk about our portfolio companies. Often we'll have a presentation, a chat with a potential investment. So, that's typically my Monday, which was today. And then the balance of the week, if I'm doing an interim VP of engineering project, which I currently am, I'm typically at that company Tuesday through Friday and running engineering. And when you run engineering, you are always running engineering,

so I'm always available. But I would be at the company typically on the other days. Sometimes I might have another meeting like I did have right before this with an individual at a company where I'm an advisor. Next week, I have a computer history museum board meeting. So kind of a few little things peppered in. And the staples are typically Icon Ventures on Monday. And then if I'm an interim VP of engineering somewhere,

there's kind of that for the balance of the week. So more than enough to keep me busy. Yes. But to a venture partner, as an engineer, I have this idea that they're all fat cats smoking cigars and having three martinis lunches. How accurate is that? That wasn't my vision. Thank you, Christopher. My vision involved sports cars.

Oh, nice. Well, you know, I would say probably or associate, whatever we call that, those are pretty standard positions at any venture firm across, you know, certainly the Valley and the country and such. Venture partner is the weirder one or the outliers. A lot of venture firms don't have venture partners. And for the venture firms that have them, it's all over the map, right? And it will range from a very loose connection to the venture firm to maybe something tighter where they're investing money alongside or with the venture firm. And it really is very per person. In the Icon Ventures case, the venture partners are

operating professionals who are part-time with the venture firm. It's not an exclusive relationship. And we add some kind of domain operational expertise. So, for example, I am the venture partner who has more of the technical ops experience. So I focus on helping evaluate companies from a technical perspective and helping on the technical side. We also have a venture partner who is more sales oriented and a venture partner who's more finance oriented. So to go back to your fat cat characterization, you know, sure, I think there are some of those, right? Definitely. Oh, and then also, sometimes venture partner is the title that a general partner kind of drops down to once they aren't as actively investing, right? And they're sort of taking a step back. They become not a general partner, but a venture partner. Or sometimes firms will start

someone who they might want to try out as a general partner as a venture partner. In the case of Icon, venture partner is just kind of a standard. We only have three of us, but we're the people more with the operating experience. So in my case, like any partner, I help source deals. I evaluate deals and am part of the investment group. But I try to focus on the technical side. For example, if we get serious about an investment, I'll go meet with the company and do the technical diligence typically. Or for a current portfolio company, if we are, say, looking to hire a new VP of engineering, I would be involved in helping to interview that person. What's the difference between what you do and what a venture capitalist does? Well, venture capital is the term for everyone typically in the VC world, but it also is often associated with general partner.

And the general partner is more the person in the venture firm who spends all of their time looking for new deals. And then once they, you know, it's more of a group decision, but decide to fund an investment, they're typically the person from the venture firm who sits on the board. And so you don't sit on the board. Instead, you work with these companies. You become part of them. Is that right? Yeah, a little bit more.

My interim VP of engineering work is separate from icon ventures but but i'm i more help out um loosely on the the technical side as part of the icon investment uh team and and then in helping you know grow our portfolio companies into you know, better companies faster. And so do you mostly work on software companies or do you also do hardware software? I mostly do software and Icon typically invests more in software. So, you know, it's a good fit for me. I typically do more software because that's my background and it's more what I feel comfortable with. Icon, you know, doesn't do much hardware investing. We're a relatively small fund, about 300 million. Hardware is often invested by venture capital firms that have larger funds,

because it tends to be more capital intensive. In my interim VP of engineering work, I have done some roles that have been hardware software, but the majority of what I do is software. And with small startups, sometimes the management, even executives, have to do technical work. And you're talking about startups that are really quite small, less than 50 people, less than 10? That I work with as an interim VP of engineering? Yeah. Okay. Yeah, I would say the smallest team that I've worked with as an interim VP of engineering, I think was, you know, one or three, you know,

like very small. And the largest, maybe it's been 80, right? And that was only one, I would say the average is maybe 15 to 20. And it's usually pretty early stage or are you coming into rescue companies at any time? Um, you know, I would say, um, a little of both, but, but typically you don't, you call me when there's a reason, right? You know, if you think of my interim VP of engineering work sort of as the hired gun, you call me for a reason, typically. The A-team. Or, you know, the current person maybe left, you know, unexpectedly or the product is late or something's not scaling. You know, they're all good reasons. But, yeah, typically you call me for a reason. is late or something's not scaling you know they're they're all good reasons but um yeah

typically you call me for a reason sometimes you call me to start things off the right way but but typically a company probably wouldn't be funded if there wasn't some some technical folks in it right sure and so do you end up doing much of the technical work like actual coding sorts of technical work typically not um you know i i i i try to keep current personally you know and when i one of the nice things about the interim vp of engineering work is i get built-in downtime in between projects. So, when I can, I'll, you know, do a iOS app or I'll try a little Angular or something, right, or do a Ruby on Rails rep, something that I think would be fun that, you know, to keep current because technology is always changing. Typically, when I'm doing the interim VP of

engineering role, though, you know, I'm making many technical decisions and helping with the people and the process side. But I would say, you know, over 90% of the time, I'm not coding in a day-to-day role with that. That makes sense. I mean, the idea is that they have, well, that they have the idea and you're there to, as you say, do something specific. Right, yeah, to help them scale or to get them to the next level.

And yeah, as you say, I think they have hopefully the right people. And if they don't, you know, I might help them get some new DNA into the company or hire a new expertise. Or maybe people aren't quite in the right roles. But often we have a lot of the right stuff from a technical point of view. So you do a lot of hiring. How do you find good people? You know, that is a tough one, right? I am often

asked that question. I would say there's no silver bullet for sure. I mean, it takes a lot of work. I source my network, right? You know, I've been at a lot of companies now. I basically change jobs every two years. I mean, my average interim VP of engineering project is roughly six months. So I do about two a year. So I know quite a large number of people at different companies with different backgrounds. You know, I've done consumer companies, I've done internet companies, I have done some hardware software companies, I've done mobile companies, enterprise, SaaS, cloud, you know, lots of different companies. But I do, just for the record, I never recruit from anywhere I've been. You know, that's just unethical, right? Someone

who worked for me, I don't know, three years ago when I was doing an interim VP of engineering, it just would never be appropriate to go source that person. But if that person has left and gone to company, you know, D, well, then they're fair game, right? Yeah, exactly. And, you know, there's all the classics of, you know, I'm a big believer that the best people tend to come from the people you have. So try to have a more than generous employee referral program in place, right? I mean, why would I want to pay a contingency recruiter 20%, you know, let's say it's $100K salary. So why do I want to pay them $20,000? I'd much rather have, let's say, an employee referral bonus of $10,000, right, which hopefully gets one of my employees attention and gets them to spend a little bit longer

combing through their network and thinking about whom they might know, right? Yes, that is so much better to have the built-in reference. It's so much better, yeah. And then when you don't, I think it's super important to do back-channel references because who would give, as one of their references, someone who would say, you know, questionable things about them, right? I think one of the great things about LinkedIn is I can see who knows who knows who about someone that I'm looking at and potentially get a good back channel reference. I'm always surprised people who give me references

who don't say nice things about me. Yeah, yeah, exactly. I'm so shocked by that. I know, I know. So it's still good to check references, even with the people they give on the list. But still, I think the back channel gives you more of the texture of what they're really, you know, like to work with under fire or in a more challenging situation, perhaps. What kinds of mistakes do you see in hiring?

Well, you don't see it as often as you used to but i think you know in in the old days right um we used to hire i think a lot on resume and there wasn't as much probing on really the technical side and i i think now that's certainly not the case right you see people doing technical challenges before they even get a phone screen. You see interviews where we're up at the whiteboard with people, having them describe architectures, do some coding that in places where they don't, I guess, challenge people as much as they should technically. Often people don't work out, I think, for fit. There's not enough time spent on the cultural fit. I see a lot of what I call the body rejecting the transplant. When someone who's only worked at larger public companies goes to a startup company.

It's not that the person's bad or the company's bad. It's just perhaps it's a very different environment and expectations are mismatched. Or there's just not as much time spent on the team aspects and the dynamics. Because especially in startup companies, right, you do spend a lot of hours with the people. And it's often under close quarters. So that fit, I think, is more important than at a larger company where there's just more space, maybe more places to hide, and more people to work with and to transfer around if things don't work out as well. Those are hard qualities to look for in an interview,

especially if you're also trying to make sure that you have a reasonably diverse workforce. That's a great point. Yeah, yeah. Any hints on how to balance those? I mean, it shouldn't be a balance. It should be orthogonal, but it's easier to feel that simpatico, we can get along with somebody who looks just like you. usually a better, stronger, higher performing workforce goes a long way. I would never hire someone or I would never personally want to be hired, let's say, because I'm a woman, if I wasn't the best candidate. Now, if there are three candidates and we're all pretty equal and two are guys and I'm a woman and we're looking for a female engineer, I'm okay if you give me that nod.

But I think we still need long way in making people think about sourcing and giving names that are more broadly or you tell your recruiters, hey, I'm looking for people who are a little more diverse, being sensitive in the interview to potentially cultural or different types of issues to make the person feel more comfortable. But, you know, there's no magic bullet, right? And do you think it comes at the name stage? You can't say, oh, of these five candidates who are all very competent and all very similar, that's not where you're working on diversity. You have to go out and find the names and say, yes, I'm interested. Yeah, yeah. Because, I mean, you know, if I weren't to raise that myth with my recruiters or even, you know, with my team for the, you know, internal stuff, I would get candidates that look like, you know, the majority of candidates already have, right? It's harder to find the culturally diverse candidates in engineering.

So hiring's hard, but it's sort of fun. There's also that image, possibly a bad one, of VP of engineering, especially the interim ones, joining a company, firing a bunch of engineers and hiring all their manager friends. Really? Where did that come from? Is this just perception and has no reality? Gosh, you know, I have to say I have, you know, I've probably done how many? Like, I've been doing interim VP of engineering work, let's say, roughly since 2000. So, let's say 16 years, two years. So, let's say I've done 32. I have never done that. But... No, but you've heard about it, haven't you? Well, I haven't heard about it with interim VPs of engineering, and there aren't many of us,

to be honest. But I have heard about it with, you know, let's say any executive, right? So if I'm a CEO or I'm a board and I'm hiring a new executive, typically one of the things that I expect or hope for is that this person has what we call coattails, right? So he or she has some people that if we were hiring, would want to work for them again, and they could bring along. And certainly, you know, in engineering, talent is tight often, and we're often hiring. So sure, I would hope that any VP of engineering that I would hire would have some people that would want to work for he or she. It's always he, would have some people that would want to work for he or she, it's always he, but you know, that would want to work for him. But typically,

I don't see people bringing in their two or three cronies. I mean, you know, I have seen that, you know, I won't say that I've never seen that. And it usually, you know, is super unpopular and doesn't work very well, right? And often that VP of engineering might not be there that long either. But then again, sometimes the reason why you're hiring a new VP of engineering is because you do need to expand or maybe you're pivoting and there's some new skill sets you need, or maybe, you know, and there's some new skill sets you need or maybe you know there's trouble in river city and so you actually need to hire two three new people in an area and you know the the person is is pulling from their network and and perhaps they're you know i i have

the advantage i guess of um although you know i don't recruit from my prior companies i know a lot of people in a lot of different places. Most VPs of engineering have been at what, two or three companies, four. And so it's, you know, more limited network, I guess. So they might not be as diverse, and it might be just their two or three buddies. Oh, that's fair. I guess I've just seen it happen once or twice. And a lot of people tell me about the new exec comes in. And it makes sense to hear that one of the reasons you hire a new exec is the expectation that they will be bringing in other good people. Now, if you're

an engineer and you're sitting there going, I can't believe I just got fired because that jerk came in and replaced me with one of his cronies. Of course, that feels terrible. Of course. Right. And sometimes, you know, at least from the VP of Engineering's perspective, there was probably, hopefully, right, a reason why he did that. But, you know, I have heard of the case where I'm just the new sheriff in town and I want my guys, right, people I'm comfortable with. I don't think that happens very often. I think that's more the exception.

But, you know, sometimes also you may hire a new VP of engineering, you know, as I said, because you're going a slightly new direction and sometimes you do, I don't know, downsize, right, or change out the skill set. So you might get rid of a few people that, you know, which allows you to hire other people in a different area or with different expertise. All right. So let's change subjects a little bit. I get a lot of email, really quite a lot of email offering to let me be subjects a little bit i get a lot of email really quite a lot of email offering to let me be on a board and i do chuck it into my spam folder where it belongs but you're a real board member um on different companies uh advisor for companies what what do you actually do behind the well-catered lunch doors?

You have a lot of imagined. I know. Some of these startups I've been at, it's just really like you people are in the cubes, you people are over here, and they have fancy lunches. It's the quality of the table. Yeah, there you go. It has to be a nice mahogany table. Exactly. Yeah, there you go. It has to be a nice mahogany table. Yeah, exactly. You know, you can you can talk to people who've worked for me. But you know, I am I am very much, you know, I believe as a manager as a VP, right? I represent my people and I work for them. I don't like to have an office if if they don't, I'll sit right out there with them. Because you know,

we're working together. I'm, you know, I'm only as good as they are. And I don't like that separation. But I have seen what you're talking about now and again, Alicia. But in terms of board member, you know, I think it's different for public boards versus, you know, private startup boards. So, let's focus on that, which I have more experience on. You know, the board members, you know, there are two classes of them or two types. There's, you know, for a startup company, there's typically the venture capitalist, the general partner who made the investment, right, from their venture firm. And you probably have one or two, let's say one person on who invested in the Series A round, and then another person who did the Series B, and maybe a third person who did the Series C. So you have a couple partners from different venture firms. And then you typically have the

CEO is on the board, and then that person isn't always, but sometimes is the founder. So, you may also have the founder on the board. And then sometimes you get an outside board member, someone with a different, you know, not affiliated with the company or the venture firm to add an outside perspective. And that will vary depending on, you know, kind of the company that you're trying to build and the expertise you want to augment. But, you know, so there might be at a startup company, let's say the board meets every two months. And it's kind of, you know, there's usually what's called the open session and then the closed session. And the open session is typically kind of reporting out on the state of the business. Often there are a couple strategic topics that are discussed.

You know, so there's the exec staff, in particular, the CEO does a lot of homework before the board meeting and typically, you know, pull together a deck, right, that they're going to present that talks about the, you know, maybe an get some traction there and then finance is always some of interest. Right. The other side of the equation. Right. How much money do we have left in the bank? And then, you know, perhaps functional updates. So often the other functional VPs are in the open session and, you know, we'll have different people speak and kind of go through the different areas. And then there's the closed session where typically it's only the board members and the CEO. And that gets, you know, perhaps a little bit more down to business about, you know, hey, these are the issues that we're seeing. And, you know, perhaps some things that they don't want to share with everyone else. And then there is often or sometimes a session without the CEO where the board members just talk. But, you know, I think a board meeting is supposed to be and hopefully is something that is helpful to the company to, you know, help a checkpoint, a milestone to help give them advice, to help steer the company. It's also a good, you know, just sort of forcing function to, you know, maybe force some decisions. But,

you know, at the end of the day, the venture folks, they give the company the money, right? And they give advice and input through board meetings, but really it's the CEO and his or her executive staff that run the company and decide what they're really going to do. I do think one of the board's more powerful functions is they're the people who hire and fire the CEO. They don't typically say, hey, I don't like your VP of engineering, you know, change her out, right? You know, they could certainly give the CEO that advice, but the CEO runs the company. But the board is the one,

once there is a board, who hires and fires the CEO. That was one of the questions I was going to ask is what kind of power the board actually has, because I've been at a number of startups and at some of them, I reached a point where I was thinking, what is the board doing? Because we're in real trouble and these are obvious things, but there's nothing changing from the CEO's message. But if the CEO is lying to them or not presenting exactly what's going on. So it does sound like the power is somewhat limited. Yeah, yeah, to be fair. Well, they hope to get more money too. Yeah, they do. And if they don't believe, right, it's not going to be as effective there.

But hopefully, in most of the situations I'm aware of, it's a really positive relationship, right? I mean, it should be where the board, if you're the CEO, the board should be more than just money. I mean, hopefully, I mean, green money is good, but hopefully they're individuals, you know, hopefully you had a choice of which firms to go with, which people to go with, and you've picked people who you think can give you wise counsel and have connections or advice or help that is good, right? And that you would value. And so, hopefully, it's a good relationship. And, you know, the venture guys don't make money. They don't do well unless you, the company, does well. So, they really are on your side. Right. And they want you to succeed. Yeah. So for the advisor role, which seems to be board member minus junior board member, I'm not quite sure how to put it.

But I sort of lucked into being an advisor and they send me the slides and invite me to meetings, but they don't really seem to expect me to do much. What should I be doing given my advisor role? Well, I'm going to give you one of those, it depends again, right? I think companies sign up and use advisors in very different ways. There are some companies that I've seen who really use advisors kind of just for their name, honestly, right? They look good on a website to say that Alicia White is my advisor, right? And she's got this great background. So the fact that she is my advisor, I must be really cool, right? You know, and there are people who, you know, have famous people on their website and they

don't really engage them very much. There are other companies that are much more active with their advisors, perhaps as a group and have, I don't know, quarterly advisor board meetings or something where they will, you know, they want you to know, kind of like the board, you know, but probably less frequently, what's going on with the company and update

and they want your advice and your help, your help maybe as, you help maybe in terms of your network or your help in terms of particular expertise. There are other times where you'll get signed up as an advisor more with a particular agenda or mission. Like I've been an advisor at different startups where my role or the expectation was that I would coach the VP of engineering and the CTO. And so that would be where I would focus. So, you know, I guess it's hard for me to answer what should you be doing

without knowing the company and the specifics, but, you know, that guess it's hard for me to answer what should you be doing without knowing the company and the specifics. But, you know, they're hopefully looking for some help from you, either generically for the company or maybe with particular individuals. So, you know, asking what you can do, right, would be a good start, I guess, or asking what the, I always, I try to be clear about the expectations of any advisor role before I take it on, right? And some advisor roles, you know, there's compensation, other advisor roles, there's not. And, you know, I'm not sure of the details about yours. Mine's uncompensated. And I think it was mostly they want me to say you're doing something horribly wrong based on my experience. And I get to see their earnings and way more information into their company, which is interesting to me from a business perspective. So it's actually it's a

great learning thing for me but I and I know that they did not have huge expectations so I'm not too worried and I'm sure if they ever called you and asked you for anything being a fabulous person you would you know be willing to help as much as you can and you know I think that's that's a lot of it unless there's there is more specific expectations. Yes. And someday they'll figure out they can use my contacts a little more than they have been, but we'll see. We're not going to encourage that quite yet until I have some free time. So yeah, you're not, you're not up for volunteering that today. Not quite. One of the things that held me back as an engineer sometimes that I had to get over as I went into more management roles was that I have a tendency to hear about something, a feature usually, and then say no or rip the idea apart because that's what I do.

I take things apart. And then later realized I could do it with just a little tweaking. Of course it's possible. The whole Scotty on Star Trek, you can have it in six days. Oh, wait, yeah, an hour is fine. And when I'm working with startups, I find that I really have to control that. Because they need a lot of yeses and a lot of getting it done. Do you see, I mean, have you had that problem? Do you have approaches that work better as far as positivity goes?

That's a good question. Well, I mean, you know, I like to think I'm a pretty positive person, you know, in general, but you are too. And I'm an engineer by training for sure. And, you know, I've written tons of, I like to think, great code in my day. But, you know, I do think as engineer, or I'll just make it personal, right? Engineers in general tend to be a little bit more glass half empty as opposed to glass, you know, half full, right? You know, because we're trained to, as you know, half full, right? You know, because we're trained to, as you say, rip things apart, find problems. You know, I think as I've

done more management and worked with more small companies, I see what you're talking about, that, you know, these people, especially the founders or the early entrepreneurs, right, they are busting their butt and they are, you know, hopefully trying to change the world or they have a big vision and they often, a little encouragement will go a long way or, you know, helping them, as you said, to look at things, you know, a bit differently. So, I guess, you know, I have maybe honed my style or changed my style a little bit to, you know, be a little more constructive or positive in my comments. And, you know, the thing that I also think about is there are so many great engineering or engineered products or projects that don't go anywhere, right? It's not always the best mousetrap that wins. It's a combination of factors and a combination of talents.

You know, great marketing can go a super long way, you know, so just because you've built something fabulous from an engineering point of view that can't be ripped apart, right, doesn't mean that it's going to be successful. So, and I also try to encourage people, well, you know, try that, right, you know, fail, the classic, you know, saying of fail fast, right, or, you know, try that, right? You know, fail, the classic, you know, saying of fail fast, right? Or, you know, crawl, walk, run, try to get something out there and refine it. I'm not sure that really answers your question, but those are some thoughts. No, that goes along with the idea of being positive without promising the impossible. So yeah, to try it, to not finish it, but start it.

Yeah, and I think, you know, especially in your role as an advisor or in mine, right? I think a lot of what they're looking for is your experience, your advice. So, you know, if someone tells me blah, blah, blah, you know, I might say, gosh, you know, that, you know, and I believe, right. You know, that sounds interesting. You know, I don't, but in my experience, you know, when I've tried that, I hit these roadblocks. You might want to think about that, right. Or, you know, give them the perspective, but at the end of the day, you know, they're the blood, sweat and tears and it's their decision. And often it is the new creative, you know, idea that's the breakthrough. So I try not to rain on that too much. But, you know, if I'm asked, I will tell them, you know, what I've

seen, the pitfalls I've seen in something similar that you're trying to do or gosh the way i've seen um that idea of yours really take off is if you try this approach right you know try to try to be helpful i've been in that position too where you have to be helpful and provide advice to a startup or a company what i have trouble with is at least for one one instance memorable instance people just serially not listening and but keeping you on as advisor and you know keep giving advice and saying look at my experience this is not going to work and then watching it not work and then so but but you have to have encountered that where you have to strike a balance between i'm positive i'm encouraging these people i'm just giving them advice.

It's not, they're not required to take it. Right. But at what point do you just kind of throw your hands up and say, well, you know, I don't know what I'm doing here. Yeah, yeah. Well, you know, I mean, I have, you know, I don't think I've ever sort of totally thrown my hands up, but hey, I think you kind of owe it to them, as you say, to give them your best advice. And that's why they're paying you or asking you or whatever. But at some point, if they aren't listening, it's either you might call them on it and say, know, I've been giving you this advice and you don't seem to be listening. Is it because you're really not listening or is it because you don't agree?

And, you know, let's have that conversation. But, yeah, at some point, I think you probably feel you're throwing good money, meaning your time after, you know, something that's not going anywhere right. And that can certainly be frustrating. That actually leads to a pretty selfish question for me, something I'm not great at. How do you vet the companies you're going to work for? I know this is part of the venture partner thing, but how do you decide this is somebody it's worth putting money behind and time and thought so so is the question

um it's not how i choose an interim vp of engineering opportunity it's how i at icon ventures how we as a team decide to make an investment or not right that's probably closer to the question okay i guess now i want both of course why be held to the question. I guess now I want both, of course. Why be held to the tyranny of the or? Go for the and. Well, let's start with the second one. So at Icon, we typically are series B investors. So we will lead the second round of investment. So typically in that situation, the company isn't

three guys and a dog. It is further along. There's probably a shipping product, probably some early customers. So we will do, you know, kind of diligence and homework and dive in on all of the people, the product, and the market. Because what you want is an awesome set of people who have developed or are developing an awesome product where there is a fabulous market opportunity, right? Those are the winners. If you only have a couple of those, you're less likely to invest. And, you know, so that means, you know, I help with ICON on understanding the technology and the people involved in building the technology because, you know, that's often a key part of a startup company, right, is the technical team and the technical vision. You know, we'll do research on the market and, you know, how big we think it is. And it's

important to look at the company's go-to-market strategy, right? Are they charging $2 and hope to sell $20 bazillion or is it $200,000, right? And, you know, kind of looking at how feasible you think their go-to-market strategy is. And then, you know, I think a lot of any investment at the end of the day, it boils down to the quality and the caliber of the people. So that would probably be the answer to the first of your questions. Is there more follow on there? I think the follow on would be, how do you get good at saying, no, I'm not interested? Well, I've seen with venture firms, because I have worked with a few, sort of two approaches. One, sometimes the venture person doesn't want to tell you no, right? Because they want the opportunity to invest later, or,

you know, maybe you solve something two days after they meet with you. So, sometimes it's like, well, that's interesting. It's not quite a fit for us, or, you know, you're too early. You know, once you've done X, Y, Z, let's have another conversation. So that's sort of the let's keep talking. It's not quite a no, but it's right. It's not I'm getting my pen out and writing the check. And other firms or other individuals are just more, you know, which I think is often more helpful. It's just, sorry, you know, it's not a good fit and here's why it's not a good fit. And, you know, give the honest feedback of, you know, sometimes it's me, not you, right? Like different venture firms often do focus on different stages of

markets or different types of sectors. So it could be, hey, your company is too early for us, and sincerely, we would like to look at your Series B. Or, you know, we're not really, you know, very expert in medical devices, so not a good fit for us. Or just we couldn't get comfortable with your go-to-market strategy. You know, we don't think based on the customers we've talked about that, you know, there's enough pull for your product at this point, so we're going to pass. Or sometimes, you know, with venture firms that they actually do have a conflict. You know, it's not a typical practice to, you know, invest in companies that you know or, you know, from the get-go where you're pretty sure are going to end up competing

with each other. And actually, from the startup side, from the times I've been asking for money from VCs, the ones who tell you no are the kindest. I mean, the ones who tell you yes are the most amazing and they're fantastic people who should be allowed to drive those sports cars. But the people who say, well, let's talk tomorrow, they are the worst. They will suck your time and energy for months on end and make you think that you have it in the bag, that you're going to get money, you're all going to get paid, and then they'll just say, oh, well, maybe lunch tomorrow, and you're just like, no is kind. That's a great way to put it. Yeah, especially when it's with honest feedback, right? And that's just their opinion, but they do have money, so that counts.

But it's their opinion. And you often learn a lot from the no's that helps you to hone your pitch or to think about things differently or just to get more conviction, right? Because I think it is tough being an entrepreneur and a CEO, right? You get told no a lot, So you have to have a pretty thick skin. And you have to be a bit of a dreamer, right? And you got to believe because people are telling you no. And if you need to take that input, but don't take it personally and try to, you know, figure out how we can make you stronger and you can keep going because otherwise you're going to get beaten down, right? So say I have a little company and we're building widgets, which I know isn't your specialty.

How do I decide to seek out a venture partner? When should I, what is it, bootstrap fund myself? When should I decide it's time to go get money? Well, my classic, it depends. But so, it does depend what you're trying to build. I mean, in general, the longer you can bootstrap something and get it further along, meaning get the product more fully built, get the team more fleshed out, get customers, you know, early customers who are using the product, right? So basically, the more you build the business on your own the more you more what i say you control your own destiny right um you'll look more attractive to venture folks hopefully you'll have more people who want to invest and so you'll get better terms

and and you'll um you know get a higher price you'll control your own destiny more i guess um but you have to balance that with the fact that a lot of people can't bootstrap because they didn't make money previously with stock from another company, or they can't afford to go with no salary or with a diminished salary because they've got a family or whatever their personal situation is. Or perhaps the product that you're trying to build is a widget. And so there's maybe a capital outlay that makes it more expensive than just you foregoing salary for six months or a year or something like that. So I think you go get think you go get, you know, optimally you go get money when you have made enough progress that you can, you've proved out, you know, taken out some of the

risk and proved out some of your technology, but also when you know what you want to do and you need that money to sort of fuel the next wave of growth. You know, often when you are out raising money, it is good to say, you know, I want to raise $15 million and I'm going to use that to both invest in the product, but I'm going to be building out the sales team and, you know, spending some money on marketing and, you know, the reasons why you're, you know, requesting the capital, right? But sometimes, you know, there's the other side. It's better to play with other people's money so if you can get it, right, when you can. But I think it's wise if you make as much progress as you can on your own

because then you're also more secure that your idea is a good idea and the dogs will eat the dog food and you can be more targeted also in the venture firm that you're trying to find a match for because it really is a match, right? It's a match of the firm and the things they invest in and the person that will be on your board. It's a little bit like a marriage. So, speaking of other people's money, something that's happened in the last few years to kind of muddy the waters of funding and getting companies started is the whole crowdfunding concept. How has that complicated things or made things easier? Has it made things

easier or is it just kind of made things more difficult actually? Well, are you talking about things like Kickstarter? Exactly. You know, I think, you know, we've looked at companies who got started with Kickstarter and, you know, for the right type of project, I think, you know, it can be a good thing, right? It can show that people are interested and it gives the, the company a little bit of money to, um, or a lot, but usually it's a little to, to build that, that first prototype. Um, I don't think it's muddied the waters too much. I think more what maybe has muddied the waters is, you know, there are a lot of wealthy, super angels, or people getting seeded.

And that's a way that, which isn't good or bad, it's just different, but that gets people capital to take them further along the way before they might go and raise the classic institutional round, right? Like a Series A with a venture firm. Are there downsides to that where they don't get the network and oversight that they might with a venture firm? You know, I keep saying it depends. Well, you know, sometimes a lot of the people who are investing are, you know, they're really smart people, you know, qualified investors, they've, you know, been a CEO, or they've, you know, they've been successful, they're, they're strong operating people. And so they can give you great advice. Other times I have seen entrepreneurs, you know, because you're cobbling together stuff, right, and you need money from whomever you can get it from. They'll have perhaps 50 people who are really friends and family who put in $25,000 or $50,000. And the problem with that is often those people aren't that sophisticated, and they can, you know, potentially be kind of high maintenance in terms of wanting to know how things are going, right? Like, if you're taking money from Aunt Sally, Aunt Sally, right, you know,

that's maybe her life savings of $25,000. And so she she's not someone who, you know, isn't maybe going to ask a lot of questions or able to give a lot of help. But I think in the Valley, by and large, the people who are taking, you know, the private angel or seed round are getting, you know, fairly good advice. And it can be helpful if you want that, you need that to bootstrap. As long as it, you know, the terms are clean and every, you know, there aren't any strange strings attached that would make it look weird to a venture firm when they come in and do the Series A. All right. So I, again, want to shift gears. You have multiple degrees in CS and math, including a master's degree. You worked at Bell Labs shortly after college and writing software. You've written

software for a number of companies and then you did management and director of software and vice president of engineering. So you've had a pretty varied career, but what advice would you have for somebody who wants to put their career on the path that you're on who wants some when they grow up they want to be you what do you suggest well um i think it you know i was always pretty driven and i um you know, well, I guess a couple things. One piece of advice, whenever I was looking for a new company, you know, changing companies or, you know, going to something initially, it was important to me that I associated myself with the, you know, highest caliber or, you know, great people, right? I would much rather be kind of not the best person at the company so I could learn instead of wanting to be, I don't know, a big fish in a little pond, right? So I tried to associate myself with people who I thought were super smart and from whom I could learn. And I wanted also to do something that I was passionate about or that I

was interested in, right? Something that would get me out of bed every day. And I think you do your best work when you're excited about it. And then, you know, selfishly, I suppose, I did want to be somewhere where I felt if I did do well, I would do well, right? That I would be rewarded somehow if I did well. So I think I did, other than Bell Labs, in general, I gravitated more to startup companies. You know, I started as an engineer. I worked as an engineer for, you know, certainly a handful of years anyway, I was kind of the engineer with interpersonal skills. So, you know, I was promoted to be a team lead. And then I, I went into engineering management. You know, I was first a first level engineering manager. Later, I was a

director. You know, later, I got promoted to VP, I changed companies to kind of get the VP job, because, you know, I had a great boss who was the VP of engineering, and I learned a lot from him, but he wasn't going anywhere. And I kind of, you know, thought I was ready. But I think, you know, doing the job for a while is a good thing. I think, you know, there are some people, you know, today who want to start right out as VP or as director, right? And I think especially in technical fields, you miss so much and you're just not going to be great, right? When you have those roles, if you haven't done the other roles, you know, for enough time that you have some competence there. And I often see, you know, in startup companies, titles are cheap, I guess, right? As I say, and there are a lot of people, which is fine, who have a title of director, but it's really a first-level management position, right?

They're directly managing people. And, you know, in the old days, right, or at bigger companies, director typically means that you're managing managers. And that jump from first-level management to second-level management is pretty different. It's different when you're managing people, engineers directly versus you're working through managers to kind of get a group of folks doing something, right? And, you know, again, do what you love. And, you know, if you do well, you know, success usually follows, I guess. But, you know But I've worked at companies that have gone under, and that's been a great experience and a learning experience. And I moved on from there to do well also. Stock is often a lottery ticket.

Yes. And when you hear venture anything or board member anything, people do start to get dollar signs in their eyes. So let me ask the indelicate question. Is it lucrative? What, the stock or venture? The venture partner and interim VP of engineering roles. It can be, sure. I mean, like, you know, let's put, let's divide it, right? So, so venture, you know, often you are compensated, there's a cash component, and then there is an equity or

what's called carry component, where you share in the proceeds of the companies you invest in, right? So hopefully you're a venture firm that has some hits and your interests are aligned with your portfolio companies that you have invested in. And different venture firms, you know, there are a lot these days. I think the waters are muddied, as you say, but there are venture firms that invest in seed, Series A, Series B, Series C. And typically, there are different levels of returns, right? If you invest earlier, it's super risky, but you could hit a big winner, right? And if you're investing much later in a company, it's probably pretty clear that it might do well, right? So maybe it's a one to three return or something, right? Whereas if you're investing in Larry and Sergey early on when they're just, you know, kids at Stanford, right? It's a one to whatever, right? But so that can be lucrative. And then as an interim VP of engineering, it's a little

similar in that I take a blended compensation, typically of cash, and then some equity in the company that I'm helping out. So I kind of build my little Debbie portfolio, right? And if the company does well, I do well, right? And I think you want interests aligned that way. But it's a lottery ticket. It's a business, right? I mean, yeah, I have been, I think, fortunate, very fortunate in my life in that, you know, I have done well. I live in the house that Netscape built, as my husband and I say. You know, and I like to think I'm a pretty smart person. I work hard. I'm nice.

I'm, you know, ethical, all those things. But there are tons of people who are as smart or smarter and, you know, work hard or harder than I do and are nice or nicer than I am who haven't done as well as I have, right? It's a crapshoot. So, you know, it's, I was fortunate and I try to keep that in mind, right? I mean, that said, if you're not playing the startup lottery, you certainly can't win, but it is a crapshoot. And I do think it helps to, you know, as I said, try to associate with people who are talented and, you know, smart and you can learn from. And also, I think it's critical that you're doing something you love because, you know, it is a crapshoot. And if, you know, you're only in it

to make money, you're probably going to be sorely disappointed. So hopefully it's a good ride along the way, right? But a lot of it is luck. So I think venture folks or anyone who fools themselves into thinking it's me, me, right? I know how to pick them or this or that. I mean, sure, you might have had some interesting insights, but it's being smart, it's hard work, and then it's luck because, you know, markets can change, geopolitical things that make something that yesterday looked super important, unimportant, or made something that wasn't very important, super important, right? Like security has, you know, it's kind of been the gift that's kept on giving for many years now because of the climate.

All right, then I think I have one more question. Christopher, do you have? I could go on for days, but I'll ponder. You figure out which ones you want to ask. We have known each other since around 2000. Have we really? Have we really? That long? Yes, yes, really.

We still look great, Alicia. We still look great. Don't we? But, and we've had this podcast for 185 episodes is what this is going to be. And that translates to, let's see, four years almost. Yikes. How long have I been asking you to do the podcast

it sounds accusatory it's going to get worse actually hi you know maybe two years maybe three something like definitely someone in your close family was on one of the first 50 episodes so definitely you knew about it oh yeah yeah i did i yeah alicia she does this cool thing no i've heard good things about your podcast for quite some time. And you went on a different podcast first. I know, I know. She used to work for me, though. So, but still, but still, I feel bad. So, you were on Women Who Code Radio on their second episode last December. Oh, Christopher, can you bail me out here, buddy?

I'll just edit all this out. What was that like? What did you talk about with her? It was fun. It was for this woman, Tara Hernandez, who used to work for someone who worked for me, but she worked for me at Netscape. She's a great person.

And we talked about my background and, you know, kind of some of the challenges that I faced as a woman and my view of women in technology and that sort of thing. I thought it was pretty interesting. And it was one of the reasons I didn't ask you about your background in depth, because if anybody wants to know more about Debbie's extensive credentials, they can go listen to the Women Who Code radio podcast. Thank you. All right. Christopher says he does not have anything more to ask you at this time. He's going to spare me after those questions.

He failed to rescue you. Nice, nice. after those questions. He failed to rescue you. Nice, nice. So actually one more from me. Have you read The Idea Factory? You know, I'm sorry, I have not. I haven't either, but I keep hearing such fantastic things about it and I wanted to know how it compared to your job there.

Ah, sorry. Well, now I'm going to have to read it, huh? It's all about Bell Labs. It sounded fascinating. Oh, yeah. I think it's all about bell labs it sounded fascinating oh yeah i think it's certainly changed over the over the years right i i worked for bell labs um in the early 80s before the divestiture so it was i think a pretty different place after the the bell companies were were broken up all right well then we should all go find that book and read it. Yes, there you go.

Yeah, whatever. Debbie, do you have any last thoughts you'd like to leave us with? Gosh. Oh, something. So something occurred to me when you were doing your opening remarks on the very same day that your, what, Hacks and Hats event is uh january 28th saturday at the computer history museum we are unveiling a new exhibit called make software change the world um and i i've you know i'm a trustee i'm on the board at the computer history museum so i have seen the exhibit and it is awesome and i am i'm very excited about it for a

couple of reasons. One, you know, the Computer History Museum has had another fabulous exhibit, which is a permanent exhibit that's been there for several years called Revolution, which sort of chronicles the history of computing and is much more hardware focused. You know, there's a Cray, there's all kinds of super cool things there. If you haven't gone, you know, check it out. But this adds the whole software component to the museum. And it's also, I think, more approachable, which is cool. And for the same price of admission, you can go to both.

So I guess I will leave you with a plug to go visit the Computer History Museum. I remember when my husband and I, you know, or I first moved out here from Michigan for grad school at Stanford. And, you know, people wanted to come see me because, you know, they were my friends from Michigan and I was in this, you know, California, which was supposed to be warm and very exciting. And they would come to Silicon Valley and they'd say, show me Silicon Valley. And this was again in the kind of 80s. And I didn't have any place to take them, right? I could drive them around and show them the building, right? Or I could say, well, let's go to Fry's and you can see these, you know, weird things, right?

But there was really nothing to do. And now when people come, I can take them or point them at the Computer History Museum. And we have an even bigger digital presence, you know, online. But anyway, Computer History Museum, it's worth checking out. Babbage machine is still there? No, sadly. I mean, it was on display for many years, but it was, you know, taken home by its owner. So we don't have that anymore. But we do have,

you know, plenty of video showing it running. And it was was cool when it was on display for many years, and it would be run twice a day. So that was that was super cool. Yes, I used to work near there and I'd go over, break, I would walk over the hill and see the Babbage machine run because it was just so awesome. It's a feat of engineering, wasn't it? Yeah. It's incredible. It's incredible.

Well, then I'm looking forward to your new exhibit. Yeah, you should go. It's fun. It's very fun. And it's different. I think it broadens our reach and it's going to show people, you know, how software is made at kind of a different level and lets people think about really all the places in the world where software really

is and how it has changed the world. Excellent. Cool. Thank you. Thank you for being with us, Debbie. Oh, you're very welcome. Thank you for the fun conversation. Our guest has been Debbie Meredith, Vent partner at Icon Ventures, interim VP of engineering, advisor to various startups, and trustee at the Computer History Museum.

I would like to thank Christopher for producing and co-hosting. And of course, thank you for listening. If you'd like to come to the party, you have to RSVP pretty much right this second. So please do that. You can go to embedded.fm and see the RSVP link in these show notes. And if you'd like to read our blog while you're there, contact us or subscribe to the YouTube channel, all that is on embedded.fm. So now a final thought for you from Leonardo da Vinci. It has long since come to my attention that people of accomplishment rarely sit back and let things happen to them. They went out and happened to things.

Embedded is an independently produced radio show that focuses on the many aspects of engineering. It is a production of Logical Elegance, an embedded software consulting company in California. If there are advertisements in the show, we did not put them there and do not receive money from them. At this time, our sponsors are Logical Elegance and listeners like you.