Meet the Operators: Full transcript of Tod Sacerdoti interview

Zaw Thet
Meet the Operators
Published in
27 min readAug 6, 2015

In 2006, Tod Sacerdoti decided to start Brightroll, which in 2015 is the largest video advertising network in the industry. Tod sat down with Zaw to discuss the key ways he scaled and grew Brightroll to a $640mm acquisition by Yahoo!

Audio of the #MeetTheOperators interview with Zaw Thet and Tod Sacerdoti

The following transcript has been edited slightly for ease of reading. To read the highlights of the interview, here is the original post in Meet The Operators.

Zaw: All right, we’re here with Tod. Thank you for joining “Meet the Operators.”

Tod: Nice to see you. Are you sure it’s recording?

Zaw: I’m sure it’s recording. I’ve done this before.

Tod: Is it ever going to be played, or is it just …

Zaw: Yes. No, it’s … actually there’s a sound version, but I think nine out of ten people will never play it, but you can use it for a transcript. We’ve obviously known each other a very, very long time. We grew up together in the trenches of the social media wars. That was, what, 2003?

Tod: 2003, yeah.

Zaw: 2003, and you’ve come a long way. I’m still trying to come as far as you have. What we want to talk about today is a little bit around obviously how you grew BrightRoll, right, because that’s your claim to fame, but most people don’t know that you’ve done a ton of other stuff as well, including at one point what was probably the largest party, promotion and event company in the city.

Tod: This is true.

Zaw: It’s true, but before we do that, we’re going to go way, way back. We’re going to try and give people a little bit of understanding of who Tod is, the person, not just the man, the myth and the legend. Let’s start when you were a kid. What was your favorite superhero, growing up?

Tod: I don’t think I was … I wasn’t really into superheroes, but I was sort of into every … every successful athlete was a superhero to me. Don Mattingly was probably my favorite baseball player, Michael Jordan was my favorite basketball player, and to me they were the superheroes of my childhood.

Zaw: Yeah. Well, they were icons for all of us. Do you have a favorite childhood memory? Imagine back.

Tod: Favorite childhood memory. Gosh, that’s a tough question. I wouldn’t say anything jumps to mind as like one memory. I would say the thread through my childhood that was probably most impactful on me was I was an insane collector of baseball cards, and so there were many moments, from being very young and getting a holiday gift of what was probably $20 at the time but seemed like the best gift ever, was the latest baseball card pack or set or something like that. Then later I actually was selling baseball cards at conventions, and it was an opportunity for me to become independent, leave the home and do something on my own, and later just being really passionate about baseball cards.

Zaw: What is the most that you ever made on a baseball card? Do you remember?

Tod: I really don’t know. I still have them all. I sold a lot of cards, but I bought a lot of cards, so probably hundreds of dollars, something like that. It’s probably not my favorite childhood memory, but when I think of my youth, the most exciting things were sports‑related things or baseball card‑related things.

Zaw: I had a couple cards that I was the proudest of. I remember I had a David Robinson, who’s basketball, but rookie card, and I had a Mark McGwire rookie card.

Tod: Yeah, McGwire and Ken Griffey, Jr, I think were the two [inaudible 03:10].

Zaw: I never got that one.

Tod: Yeah. I actually don’t know. I got my dad’s collection, so his were totally destroyed from a quality standpoint because he actually put them in a bike wheel, but I would say some of my favorite cards were just my dad’s cards. I didn’t have a Maris or Mantle, but I had a few other ‘50s athletes, which was fun. Ken Griffey, Jr. was, when I was a kid, the rookie that really changed collecting.

Zaw: Yeah, absolutely. Okay, now let’s step back to later in your career. As you’ve gotten older and you’ve started to … you know, you read, obviously, a ton, and you’re a student of history … is there anyone in history that you would most like to meet?

Tod: Anyone in history that you would most like to meet?

Zaw: It could be … let’s go with a real historical person, not fictional.

Tod: The people that I’m most drawn to are the inventor types, like the Edisons, the Teslas, the people that were tinkerers and inventors. Those are the people that I find most fascinating in history. I don’t think they’d be anywhere near as interesting to meet as they appear in books, but I think those types of people. I don’t know if there’s one specific. Let’s say anybody who was a prolific inventor … Ben Franklin … over their life, would be interesting.

Zaw: Da Vinci? Sure. Okay, cool. Okay, let’s segue into running businesses and the true operator. Tell us, before the acquisition by Yahoo, how big … with BrightRoll, how many people were you managing or hired up to?

Tod: Yeah, we were slightly over 400 people when we were acquired. We were hundreds of millions in revenue. We had been profitable for four years. We had about 13 offices, two outside the U.S., and I think those were the kind of metrics.

Zaw: We talked a little bit before this, and you had said you felt like BrightRoll really was an execution play as opposed to having some other kind of wind in your sails. Why do you feel that way?

Tod: There was an epic meeting in the history of BrightRoll where myself and the head of product and engineering were … I think this was three years before the acquisition, and just saying, “Okay, is this going to be like an iPhone category, where someone’s going to invent something that just changes the trajectory of their success and everyone else will be left behind, or is this going to be like an execution business where there’s a large surface area that you have to continually add value to, but you’re never going to kind of 10x the category and invent something that just changes everything”? I think that it’s really important to know which type of category you’re in. Of course, a lot of times people think they’re not in an iPhone category and then get innovated around, so it’s actually pretty hard to know for sure.

My assessment was this was going to be a blood sport category, where it was a huge amount of surface area, competing every day, a relatively narrow feature war and customer‑by‑customer battles, and as such, execution was going to be really our defining characteristic. Of course, you have to innovate as well, but I just didn’t think there was going to be this singular innovation that changed everything. That essentially changed how we went to market, it changed how we hired, it changed how we invested, but I think it was true for us in retrospect.

Zaw: How did you communicate that to the team? Obviously execution is important in any business, but that being the primary focus, how was that related to the rest of the organization?

Tod: I think everything starts with strategy of the company, and our strategy wasn’t we’re going to put every single resource on innovating in this one area. It’s like here are what we ultimately defined as three strategic areas we were focused on and we’re going to make significant investments in each, and as a result we’re going to be spread really thin. The downside of that is we may never have the clearest number one in any one category, but as a result, we think that’ll let us win over time.

I think you have to convince folks that that strategy makes sense, and there’s a lot of … it’s all tradeoffs, but I think getting people behind that vision was what ultimately led us to being able to be successful.

Zaw: Did you end up having to swap out any of the members of the team?

Tod: Not initially. Eventually I did bring in a COO who reorganized the company, and by going after a large surface area and having multiple business lines, ultimately we decided we needed single owners in each business, and the people we had in place had signed on for being GMs of everything. I think that’s a logical point at which companies mature, but we didn’t do a ton of swapping early on as a result of that decision.

Zaw: We’ll talk a bit about hiring, because obviously that execution play related into hiring. Did it change the type of people that you hired, or were you looking for specific things in your hires? How did you go about hiring with that in mind?

Tod: Well, I think it depends Are we talking about engineering hiring or are we talking about hiring in general?

Zaw: Yeah, in general.

Tod: Hiring in general, it didn’t necessarily change what we were hiring, only in the sense that we weren’t looking for people who were going to come in and we would give them a project, and they would work entirely on their own and invent something new. We wanted people that were going to be very knowledgeable of the category we’re in, understood the competitive landscape, understood how to incrementally differentiate our platform versus other platforms, and every week or every development cycle, figure out how to add value to our platform.

That’s a very different, and it’s somewhat less attractive. Certain people want to be given a project, like, “Go, conquer a new market, think about it completely a new way, and you don’t need to worry about what anyone else is doing because you’re essentially inventing the future,” and that’s exciting. Personally, individually, I love doing that, but that was not the business that we were in. In that sense, it would impact who we hired.

I think from a product and engineering standpoint, we also didn’t have multiquarter invention processes, so it wasn’t like go into a new market, pick a new technology, completely think about this in a new way and come back with a new, innovative solution. A lot of it was incremental feature development, and again, that’s just a different skill set and a different area of interest.

Zaw: As you guys were thinking about your hiring plan for that, were there specific questions or ways that you would tease out whether that person was suited for what you guys were looking for?

Tod: Yeah. We spent a lot of time nailing down the definition of what made somebody a BrightRoll person, from a cultural perspective. Two of the elements of that were really collaboration … so someone who really does like to work with other people in the company … and we call it GSD, which is Get Shit Done, so very execution‑focused. During the interview process, we would, in addition to other things … you know, passion and transparency were really there too … we would try to tease these things out.

If someone wasn’t what we would call a GSD person by nature, that just wasn’t a good fit for us. It doesn’t mean they’re not a good fit for business, just not for our company. I would say it became very clear, when somebody joined the company, did they fit into the GSD culture or not, and it was a filter for us up front. It was a terminatable … I don’t know if that’s the right word … offense if you were not that way once you were here. If you did not focus on execution, we just weren’t interested.

Zaw: A lot of companies, especially if they’re growing, are trying to do what I think you’ve done and build out the set of core values that especially they look for on the hiring side. Maybe you don’t remember, but building up the passion, transparency, collaboration and getting shit done, what was the process to build that out, because that’s not the easiest thing to translate into only four characteristics.

Tod: How did we create the four, do you mean?

Zaw: Yeah.

Tod: Well, I always think your culture is … when you think of your values, it’s like a reflection of reality rather than an aspirational role. I think when we actually decided to narrow down our values to those four things, based on when we ramped up our hiring process, we were starting to hire inconsistently, so it wasn’t like the other way around where at the beginning of the company, we said, “Here are the four things that matter.” It was more we started ramping up hiring and said, “We need to have a clear filter in the hiring process, so let’s discuss what is the reflection of our culture in terms of values.”

It’s a little bit of a backwards process from how you would traditionally think about it, and it was driven by our head of talent, who said, “I need the values clearly defined, because I want the hiring process to reflect that. I want the questions we ask in the process to filter for that, and I want to make sure that we’re authentic about those things in terms of how we reward and potentially terminate employees.” To me, the best measure of culture is do you terminate somebody who doesn’t comply with it. If you don’t, then it’s not really your culture.

One of the examples that I think I recommend to other companies is make sure that your hiring process, the actual process itself, purely, to its core, reflects the values of the company. If you value getting shit done, then they shouldn’t be waiting for a response for two weeks in the middle of the process. If you value getting shit done and execution, that person should say, “Wow, I sent an email in and I got a response in 24 hours. I went in to the interview and I got feedback in 24 hours.” If transparency is a value, I should know exactly where I am in that process, like what gates I need to get through to get the job. I also would expect to have very clear feedback after every interview session or gate in the process in terms of how I did and where I stand.

We got a lot of responses from people that interviewed at BrightRoll that it was actually the process itself that convinced them to join the company. They might have heard about us because of the “TechCrunch” article and they saw us on LinkedIn, but it was actually the interview process that convinced them that it was a company they wanted to join. To me, that was the sign that our process was working, because we did lots of things during the process to demonstrate our culture to people. If they were drawn to it, then they were probably a good fit, like little things.

One of my favorite things that our head of talent did was there was a single talent person assigned to your interview process. You had a single person who was shepherding you through the process. When you would show up for your interview, the person was waiting in the lobby in a chair to greet you. Actually, they weren’t even in a chair. Usually they’d be standing there waiting. You’d walk in and it would be like, “Hi, Bob. It’s so great to see you. We’re really excited to have you come interview,” and people would be like, “Holy shit. I’m used to going to the front desk, asking for the contact, sitting there for 15 minutes, like that awkward interview. You’re in the lobby and you’re looking around, you don’t know anyone.” There’s just so many things about the process that are awkward.

This person would greet you right up front. They’d be waiting for you. They’d walk you around, they’d introduce you to a few people. You felt super‑welcome. At the end of the process, they would greet you at the end of the last interview. They would walk you out. They would say, “Listen, I’m going to talk to the team. I’ll going to call you in three hours and I’m going to give you the exact feedback from the interview process.”

They would go and do a retro on the candidate, and they would call and say, “Here’s the feedback. Here are the things you did really well, here are our concerns. There’s concern that maybe you’re not as technical as we thought, or maybe … “ and really give them the positive and negative, and people would be like, “Holy crap. If this is what it’s like to work here, that’s the kind of place I want to work.” It’s just a very different process from any interview process I’ve ever seen.

Zaw: I don’t think I’ve ever heard of an interview process like that, which it should be more like that. Did you guys use software to collect this stuff? Did you build a system internally? I don’t know if I’ve heard of a system that people use for hiring being able to handle this or support it.

Tod: We ended up using a software package called Greenhouse, which I think has now caught on. It’s pretty popular in the Valley. Before, we honestly did everything in Google Docs and it was managed manually. Once we got to a certain scale, it became hard for the talent team to push that out, but the talent team originally was build only around products and engineering hiring, and we just weren’t processing that many candidates. I think we hired … in the two and a half years that team existed, we probably hired 50 to 75 people, so it wasn’t like an unbearable process. Once they started owning everything, then we needed the software [inaudible 16:27].

One anecdote that I always share is our head of talent said, “You know, every single person we touch in the hiring process, from an email out or a LinkedIn ad or someone who comes into one of our … “ we did a lot of on‑property events, “ … to somebody who comes and interviews who gets turned down, every touch is a branding event for our hiring process.” If you actually map it out, the single largest segment of people you touch will be people you never interview, and the second‑largest segment will be people you interview and turn down. The people that actually … like you interview and you give them and they accept, will be the smallest segment of people that you touch. You really need to think about the broader touch points in terms of having a positive impact, as much as the people who you absolutely hire.

The segment that we focused the most on was people that we interviewed but didn’t hire, because our hiring ratio, offer ratio, was probably less than 10 percent, right, and I think it depends on how many people … what gate in the process, how high the percentage got. One of the really big criteria was if we interview somebody and we decide they’re not a fit, it’s a very large segment of people we touch that will be very vocal about your company. It was really important to him … and he convinced us all it was really important to the company … that those people had a great experience.

In the end, when we mapped referrals, we actually had more referrals from people we turned down than from any other segment other than employees. If somebody goes through your interview process, you turn them down and then they refer you a candidate, to me that’s a great sign that (a) the process is working, your culture is coming through, but (b) it’s a very low‑cost referral channel, just like existing employees are. I think out of the 50 or so, we probably hired five to seven folks through referrals of candidates we turned out, which is just … you know, it’s like a free channel. I think there’s no reason … if people you turn down are having a great experience, it doesn’t cost you anything, right? Again, if that’s part of your culture, that reflects in the interview process.

Zaw: If you are going to do it all over again a couple years down the line, either your next company or another company that you help start, what would you change from day one? What would you put in place from day one? It’s obviously different when you’re a five‑, ten‑ person startup than when you’re a 500‑person company.

Tod: Yeah. I would say, first and foremost, having a mission from a company perspective that … and I don’t mean like your company mission. I just mean it in the sense of your company stands for something that a large number of people care about, is really a good filter if you’re looking for different areas to focus in a business. We were an advertising company, and so our mission as a company did not necessarily resonate with a large percentage of the population.

I would say first and foremost, it’s a huge advantage if you start a company in a category where your mission is something a large number of people are drawn to. That’s a huge advantage in the hiring process, like number one. I would say number two, knowing who you are, which whether it’s culture or values or something looser than that mission, really does help you filter the process.

We had a speaker come in who runs a company called Madison Reed, which is a female haircare‑focused tech company, and she said, “We talk a lot about love at the office. We love our product, we love our colleagues. We want to work in an environment with lots of love.” It’s like that’s a clear filter. If someone comes in and says, “I don’t want love at the office, that doesn’t resonate with me at all,” that’s great. Then they’ll stop interviewing, right? Knowing who you are in terms of being able to express that to candidates really helps you filter in terms of knowing who should be a fit. I think it’s like know who you are and express that in the process.

I think the third thing is the process should really, really, at its core, reflect the best things about the company, and I didn’t really appreciate that at all. In my prior companies, I always remembered we felt good when we turned a candidate down because we felt like that showed to us how high our bar was, and I think that’s really the wrong lens. It’s fine to turn people down, but you should make sure they feel good about that process as much as you feel good about that process. Any personal or corporate value in turning other people down or being … or displaying your high bar I think is really a negative lens and doesn’t have a place in the hiring process.

Then, I think you need a single person responsible for the hiring process and be accountable for the results, and we were late in bringing that person in and finding the right person.

Zaw: Good. That makes perfect sense. Obviously you’re really proud of your hiring process and the team that you’ve built. What were, do you think, some of your other keys to success at BrightRoll, in terms of operational or ways that you manage the business?

Tod: I think the thing that … people always say, “Why were you successful?” I think number one was focus, and focus was in a huge amount driven by the fact that we struggled raising large amounts of capital in the beginning. It’s the classic story of poor us … and this doesn’t apply to everybody … but poor us. Not having a lot of resources, people, engineering talent, money in the bank, et cetera, really forced us to be extremely frugal and focused. Of course, when we reflect, that was actually our greatest strength. Many companies we competed with early in our trajectory had more money, more people, more marketing value in the category, and those things really ended up not being turned into lots of long‑term value.

I think, your default being no, like, “No, we’re not going to do that, no, we’re not going to expand into areas that aren’t core, no, we’re not going to spend money on these,” having that bias of we’re only going to do the very few things that matter, and being ruthlessly consistent in that perspective, became a huge advantage. Anecdotes about that, there were lots of people trying to innovate in video advertising around different ways of selling and different ad units and different ways of pricing, and lots of companies tried to expand into areas.

Our core was, “Television is a $7 billion market. It’s one ad product. It’s really simple to understand. People are already buying it. Let’s just focus on moving dollars from what people already know into the digital category, and just never veer from trying to change the way people buy media,” rather than just make the way they buy media much more efficient in a new category. We were just laser‑focused on that. I could go into the nuances of that, but I would just say don’t try to change too much, particularly in a category that already has a channel that’s working. It’s just focus on the areas in which you can add value, and that was a huge part of our success.

Zaw: As the CEO, how much time did you devote to the sales process, in terms of working with the clients? Some folks carry bags a little bit, some folks don’t get involved at all and let their VP of Sales or CRO handle it. How do you see your role in the sales process?

Tod: I think the best CEOs in technology companies are people that can straddle the line between sales and product and engineering, and we talked about this in our pre‑interview. I think … and this was the quote from the Mark Leslie business school … you know, the sales team and the engineering team are the drivetrains of the company, and everyone else, including the CEO in the company, supports those two organizations.

This isn’t 100 percent true across Silicon Valley, but I used to say at our sales conference … I would say, “My job is to make the sales team feel like we’re a sales‑driven company and everything is about sales, and I’m a salesperson and sales is what matters, and we’re going to focus on the sales [inaudible 24:41] first and foremost. Then when I talk to a product and engineering organization, you need to make that team think that we’re a product and engineering organization. All that matters is, you know, software development and best‑of‑breed product engineering processes, and we’re going to temper the sales team’s enthusiasm and make sure they’re supporting product and engineering,” and I would say that all with tongue in cheek, because both teams knew that I was saying that to the other team.

I think that, particularly in the media category, we really do straddle the line. It may be the same way enterprise software does, if you think about coming out of Salesforce or B2B business, because we are a B2B business, right? I sort of tongue‑in‑cheek made those statements to those teams, but on a personal level, I had to do that individually. I needed to go to sales calls. I needed to be in front of customers, and when I was in front of them, I would tell them, “I’m not the sales guy. The sales guy’s sitting next to me. I’m the product and engineering guy, but I’m here because I want to hear your feedback. We want to build products that drive value for you,” and it let me have credibility in the sales meeting as not a salesperson.

Of course, when I would go to the product and engineering offsites and shragging sessions, I would say, “Let me tell you about the revenue of the business. Let me tell you what customers care about. Let me tell you how somebody who’s in the product, using it to drive their business, speaks and feels and experiences our product.” I think that if you can straddle that line, you can really drive I think more value than someone who is best of breed in one but can’t understand the other side.

Now, of course that happened to be my background, so that was where I was biased. I don’t think you have to be that way to be successful. I would just say if you’re not that way, you really need to hire people that can counterbalance your skill set.

Zaw: That makes a ton of sense. When you think about the other functions in a company, if you think about marketing, obviously Silicon Valley is a very product‑ and technology‑driven area. How do you think about treating marketing? Was it just to support sales and drive your customers into the top of the funnel? Was it product marketing, in terms of helping to define new products? Where did marketing fit for you under the rubric?

Tod: I think that when I look at our history, marketing, we did okay in marketing, but I would never say it was an area that we really differentiated in and won versus our peer set. When I look at our peer set, I also don’t feel like anybody was the 10x better than the category on that. I don’t know if our category is just a really hard category to break out in marketing, or just nobody’s done it well. I have a hard time having a lot of strong advice in that area.

I guess I would say that what ultimately really worked for us was driving as much of our marketing value in ways that weren’t paid. We did a ton of things like contributing articles or speaking, or content that we created. We were never really successful at spending money in terms of generating needs or value. I think in the media business, so much of the business, it’s a small customer set, very high ticket price … you know, millions of dollars per client … and you’re just not going to win those businesses by creating an online need or by doing some support of [inaudible 28:10]. I just think in the B2B marketing, in the category we were in of media, marketing wasn’t the defining characteristic of the winners.

Zaw: You’ve got all these different functions that report up in to you. How do you manage or did you manage your day‑to‑day and week‑to‑week interactions with the team? What was cadence in terms of getting reports, getting updates, meeting with the team, and how did that maybe change for you? Did you find the best balance?

Tod: Yeah. I mean, I think that there are few things that I believe to my absolute core, and that’s because they worked for me. I was very much a fan of the weekly meeting.

Zaw: Weekly meeting with …

Tod: Monday morning, the entire team that reports to me, and eventually we had a few people that didn’t report to me. The operating team that’s running the business, being super‑clear and transparent within that team about what’s going on, and then doing one‑on‑ones with people that report to you and being religious about them during the week, every week. Those were the two things I was absolutely core to, and then we did an all‑hands with the whole company once a week, and then eventually that became an every‑other‑week, once we were over a couple of hundred people. Those were my cadence of communication.

Zaw: How did you manage those meetings? Were you getting reports in those meetings? Did reports come in prior? How did you manage that?

Tod: We followed this model of we wanted everyone to disseminate up, all the way up to me, and then disseminate down in a weekly cadence. I wanted to have everyone report up as to what they were working on, progress, anything they were blocked on and a current state, and then we would report down any decisions that had been made, changes, overall strategy, et cetera.

We had our Monday meeting basically split between dissemination … basically all the departments sharing out state, progress and anything that they’re blocked on … and then we would have a part of that meeting in terms of decisions that need to be made, things we were blocked on, how we were going to resolve them, state of things that only I or a limited number of people would know, like capital or the board or anything like that, and we would just pulse that up and down every week.

I would say at certain times we were … that meeting needed to be much more around a decision‑making meeting, where there were really core issues that we had to address, and there were times at which that meeting would be much more of a dissemination meeting around state and understanding what other teams were working on. That meeting changed at different times, from an hour meeting that was mostly decision‑making, to an hour meeting that was mostly dissemination plus an hour that was decision‑making. It fluctuated over time, and I think that was just a reflection of where we were as a company. We always had both dissemination and decision‑making done on a weekly basis.

Zaw: How did you set goals for the team? Was it weekly, monthly, quarterly?

Tod: We did quarterly. I’m sure there were times we were short a time frame, but we eventually moved to more of a quarterly cycle, and we’d follow the objectives and key results process where some of those would be top‑down and some of them would be bottom‑up. We would make sure that everybody … if there was anything shared among multiple teams, it was goals on multiple teams.

We would grade ourselves every quarter in a public forum, and we would share that across the entire company, and then actually we did that through the entire organization. Every single person in the company had publicly‑disclosed quarterly goals, and their grades among their performance was shared. It wasn’t tied to their compensation, we just wanted a transparent goaling and grading process to hold each other accountable.

Zaw: How did you think about failure in the context of goals? Google’s famous for having people trying to target 60, 70 percent accomplishment.

Tod: Yeah. We replicated that model. In the beginning, it was very hard for people to be comfortable with failure, but I think ultimately we … people got comfortable. I would say our average was more like 50 to 60, so either we didn’t do a good job or we were successful getting all the good stretch goals in. I think that was generally our actual average.

Zaw: How far ahead do you think a CEO should be thinking? Were you thinking a quarter ahead, a year ahead? What was your typical?

Tod: I do think it depends on where a company is in its maturity, where the category is in its maturity, and where the competitive set is. I would say now, in reflection, I think startups actually have an advantage … which is super‑ironic … in being long‑term thinkers. If you think about it, startups are being capital‑constrained and you’re thinking about how you’re going to meet your burn rate in 12 months, but on the flip side, public companies and companies that are measured on profitability and EBITDA multiples really do have a hard time thinking far out. I didn’t really think about at the time, but I think we were always thinking a few years out, and I think that was a huge advantage for us in retrospect.

I think, as a CEO, you should have clarity a year out, not perfect clarity but a sense of where you want things to go. I think you should be thinking a few years out, but I never did any real work more than a year out in terms of defining strategy and roadmaps and things like that. I think in my mind I was always saying, “Where is this going to be in a few years,” but we were very clear in a quarter, a sense in six months, clarity but nothing really documented over the next year, and then at an individual level I was thinking beyond that. That’s how I think about it.

Zaw: That’s great. Any parting words of wisdom for entrepreneurs out there? They’ve raised money, they’re growing their business, but they’re now thinking about taking it to the next level. What would you like to impart for the next generation?

Tod: I guess my number‑one takeaway … and I said this. I’m not sure I believed it, but I said this when I started BrightRoll, which was the only way really to be qualified to be an entrepreneur is to have been one, right, and I would say the same thing is true. The only real way to be qualified to be a CEO of a 500‑person company is to have been one, right? There’s no real … I mean, of course you can always gain more skill sets, but there’s really nothing like actually doing it and being in the seat. If you take the risk and you start a company and you raise money or don’t, and it fails, the irony is at least at the end of the process, you’re then qualified to do it.

My advice to folks is don’t get so wrapped up around the axle, around am I ready or am I qualified, because it’s like I think the right thing to do is essentially dive in. There’s so much support for failure in Silicon Valley, that the irony is it’s the greatest set of experiences you could ever have. I just recommend you don’t be dumb about what you pursue, but take risks, dive in, and at least at the end, you’re qualified to do it the next time.

Zaw: What are you most excited about for the future, where the Valley is heading, where technology is heading? What are the things that are getting you excited now, that you may be moving out of advertising at a later point, a couple years?

Tod: I don’t know if there’s a single sector or a certain area of investment. I think it’s such an exciting time, but the bar of risk … you know, going back to my prior comment about taking risks … it’s so much lower risk now on so many levels. There’s many ways to be successful. You need a lot less capital. There are so many more resources for entrepreneurs. There are so many more angels that can be sources of money but also sources of support.

I just feel like it’s just such a great time to be an entrepreneur, bubble and frothiness aside. I’m just excited that the model that has been honed over the last 20 years is just humming. I think it’s an exciting time for entrepreneurs.

Zaw: Awesome. Thank you for coming on “Meet the Operators.” We’ll have you back in soon.

Tod: Absolutely. Thank you.

To take a look at the highlights of the interview take a look at the original post

Postscript

This is interview #1 of what I’m calling “Meet The Operators” or MTO for short. The mission is simple, to allow anyone to learn from some of the best in the business on how they scaled their company or organization to success. As an entrepreneur turned investor, I’m constantly getting asked for advice from my portfolio companies and others. Turns out, I don’t even have a small % of the answers. So, I turned to my network and started asking them the same questions. Interestingly, some of the most interesting conversations and answers came from leaders outside of tech (military, science, music, government, NGOs, and more) — whom you’ll hear from as we release more interviews. We’ve got a full slate of interviews queued up and ready to go, so please follow MTO on medium and twitter to stay up-to-date with the latest and greatest!

I fully agree with Reid Hoffman’s now infamous quote that, “if you are not embarrassed by the first version of your product, you’ve launched too late.” Well, consider this the first alpha release of MTO. It’s far from perfect, but I wanted to get it out. At Signia, we pride ourselves on having built a firm that strives to be the most helpful investor that an entrepreneur can have. I believe that should apply to not only companies we’ve funded, but also to the ecosystem as a whole. This is one small way I want to give back to an industry that’s given me so much.

Big thanks to Rahim Noorani, my rockstar intern for the summer. I expect big things out of him, so please give him a follow. Also, thanks to the rest of the Signia team for their feedback and support.

Enjoy,
Zaw

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Zaw Thet
Meet the Operators

Veteran Entrepreneur, Investor, and Philanthropist -- Co-Founder and CEO of Exer (@movewithexer) // prev Founding Partner @SigniaVC