Hope Cochran on the Entrepreneurial Journey – Hers! (Encore)

Going back to the archives to bring forward one of our most popular episodes which is a deep dive on Hope Cochran’s journey to investor, public board member and colleague. She tells the story of being overlooked at her first job which spurred her to take a post in a small European country in her early 20s to take on a huge challenge. That spirit of adventure and ambition set her on the road to entrepreneur, CFO, and founder advocate. Dan Li, who is now a CEO of a new stealth company, Plus, sat down with her to learn her story.

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Transcript (this is machine driven transcription so expect some typos)

Dan Li: I’m really excited for our interview today to get the inside scoop on one of my mentors here at Madrona, who is an amazingly accomplished operator now turned VC.

Running through a quick bio, Hope Cochran joined the team at Madrona in 2017, after moving back to Seattle from London, where she was CFO of King Digital.

Hope was brought on as CFO of King to help the company go public. And then she ushered the company through their $5.9 billion acquisition by Activision. Before that Hope was also the CFO of Clearwire, Evant and the founder of SkillsVillage. She’s on the board of some public companies as well, like New Relic, MongoDB, and Hasbro.

So basically, she is pretty awesome. But today, we’re not going to spend time talking about awesomeness. We’re going to try to spend some time discussing those moments of truth that got you from here to there.

Recently, Hope and I were on a little field trip to visit a company and we were asked, so what really gets you up in the morning? This is particularly topical today because we’re talking about Hope enjoying getting 4:00 AM calls, because those are the ones that you really need to answer. So, while I was thinking about my answer to this company and about how cool it is to meet with new startups and inspiring founders, Hope cheekily answered something along the lines of, there’s an enormous constellation of people all around me that depend on me every single day.

So that’s definitely how I feel working with you now as well. And specifically, I feel like your ability to deal with rough times while remaining calm is a skill that’s probably been developed over a pretty long time. So today for this interview, given all of the success you’ve had in your career, I thought it’d be really fun to go back in time and talk about some of those moments where everything went wrong and how you went from chaos to success.

Hopefully, that works with you.

Hope Cochran: That would be great. I have a lot of content in that area.

Dan Li: Great.

Okay. One of the things that I think is great these days that you can go up and look up senior executives, LinkedIn profiles, and they’ll just say stuff like CEO, 2015 to 2019. It’s great. It’s like their whole career began when they became CEO a few years ago.

And it’s that’s not how LinkedIn works. And if you check out the CEO of Microsoft, it might look something like that. Anyway, I love that your profile really shows each of these transitions between different experiences and your career beginning at Deloitte and a few years later, starting a company. It’s really great for those of us coming from a professional services background, as well, and seeing that we can one day do something useful. Can you take us back in time a little bit and talk about how an opera singer and music major ended up joining an audit firm?

Hope Cochran: Absolutely. Yeah, that was an interesting choice in my college career was to choose to do a double major both in econ and opera.

And I laugh back to that decision because as I think about that, I really did it because I am by nature cheap. As I embarked on taking music lessons, I could not imagine, not taking music lessons. And if you joined on as a major, you got to take them for free. So, I signed up as a music major and took all of my music classes for free.

And then felt guilty a couple of years in and realized I actually better complete the major. So, I ended up graduating with the econ and the music major. And the only reason why I think this is pertinent is because as I think about my career, I do think the econ major got me interviews and therefore it was impactful in getting my first job. But as I think about my career, it’s those skills that I developed singing that I really feel like I utilize every day. You mentioned that I’m decently good at being calm in chaos, and I’ve been through a lot of chaos. So, I think I’ve developed that skill over time.

But I actually think I learned the basics and fundamentals of that by being on stage, because you have to learn to handle every crazy thing that’s thrown at you. Like it’s just part of the process or it’s part of the plan. So, when I think about the music degree, practice makes perfect, making sure you’re prepared for everything that you do.

Also, when things do go wrong, handling it calmly and working through it, like nothing was wrong. And so those are some of the skills that I really take with me throughout my entire career. And so that was a pivotal part of my journey. And you’re right to point out. I started at an audit firm which, that sounds boring, but you can learn great skills in an audit firm.

You learn how to manage your time. You learn how to manage your career. You learn how to be in lots of different situations. I saw a lot of problems. I got to figure out how to fix them and you get a lot of responsibility at a young age. So, it was actually a great place to start out. One of the things that was unique, in that, is I went to Ljubljana, which is in Slovenia, for a year and took on that challenge to help that country get their accounting principles in place and work with them. And that was a great learning step in my journey to then take back to the United States. One of the things we think in the United States is that the accounting laws are complex and overly thought through. And when you’re in a country where there actually, just at nascent stages and not thought through, you realize how quick they are to be ineffective. And so, I appreciated the complexity of the environment that we’ve created here in the United States.

Dan Li: That’s funny. So, I think a lot of people wonder when’s the right time to make that leap, or they’re already on the other side and they’re wondering if they made the right choice. You’re working in Lithuania and doing, I think some professional opera performance on the side, as well at that time. How does that turn into I’m going to start a company?

Hope Cochran: Yeah. I tend to be a person that tends to run towards a new adventure.

That’s just part of my DNA, so I don’t do things twice very well. And as, I looked at every step of my career, it’s always been something I haven’t done before. And when I started my company Skills Village, I was actually with PeopleSoft at the time. And I had a friend who had a great vision, and I was excited about that vision and leapt into it.

And quite frankly, leapt into it without a lot of forethought. Like we didn’t do a ton of research. We just trusted our gut that we knew that this was an opportunity that no one had filled and that we had the technical and business skills to tackle it. I look back on that with such amazement because we had such naivete, like we just thought we could get it done, which I think is a really important trait to an entrepreneur and that they think they believe in themselves and they believe they can climb every wall.

But I remember raising that first $3 million from a venture capitalist with an ID on a PowerPoint. And I look back on that moment, like, why did he give me that money? Like I didn’t really have much in terms of my background, but somehow, he believed in me as well. One of the moments I think through in starting that company is when you’re negotiating a term sheet, there are a lot of technical terms that you just don’t know unless you’ve learned them.

And I remember having to negotiate real time with him. And I had no idea what preferences were or what different terminologies were in the term sheet. So, I pretended I had to go to the bathroom, and I ran into the restroom and I called my lawyer, and I took copious notes really quickly.

And I went back in there, from the bathroom, and I went in there with all the confidence in the world that I knew exactly how to negotiate this term sheet for the first time. And he was very kind. So, I look back on that moment as I thought I was great, but really the person across the table was fully aware that I didn’t know what I was doing and helped me through that process.

Dan Li: Cool. So, it sounds like you had a great co-founder, you were able to raise some venture money. A couple of quarters after raising the $3 million, were you thinking, oh, this is great, or was it more of a, oh no, what have I done?

Hope Cochran: I remember, um, right after we raised the money, we, the first thing we needed was offices and I had to go figure out how to get an office and how to get desks and how to get chairs.

And so, we went to Costco and Home Depot. And I just remember that moment of, oh my gosh, what am I doing? I am spending someone else’s money, so we can pursue this idea and it is a moment of truth and a moment of fear, but we did believe in our ideas. So, we grew that company from the two of us to a hundred employees.

It was eventually bought by PeopleSoft. And as I think back to that. From the outside, looking in, it all looked like a success and yes, the investors are happy and all of that. There were so many moments in that journey where it should have all fallen apart and fallen apart because of decisions and things I did.

And so that’s an, and I do think that part of your journey is luck. And part of your journey is fortitude and courage of which I think I had both, I think I had luck and I had perseverance and fortitude. I think about things like I had a marketing manager who went to the local ball game and he committed $250,000 of marketing money.

To market Skills Village at that ballpark. And we didn’t have 250,000. I mean we did, but like I had every single dollar planned out and he came back so proud of himself and I was just panicked. And somehow, we had to rework the budget, we had to rework everything because I couldn’t get out of that contract.

He signed it; it was legal. And I had to tell my board, I was embarrassed. I remember another moment where we needed a new office space, and it was the Bay area. And I signed a seven-year lease at astronomical rates, and I didn’t think twice about it. But when it came time to be acquired, it was that lease that was the noose around our neck. Meaning the amount of money that was committed and the company buying us didn’t need that space. That became a material issue in the acquisition that made the acquisition almost fall apart. And so now I look at those leases differently. How did I get out of that mess?

I went to that landlord on my knees. And I begged for him to give me forgiveness and he was kind, and he did, and I don’t know why he did. He had no reason to do that. Wow. But he saved that acquisition. And again, looking from the outside in that acquisition looked positive and everything was fine, but there were so many moments that it shouldn’t have happened.

It also was in 2001, when everything had crashed and the company had asked that was acquiring us, that we pay all of our payables right before the acquisition happened. And then the market crashed, and I was left with no cash. Like why did I agree to pay all my payables before the acquisition happened and leave myself with no cash? I did because I was naive.

And once again, someone was helpful to me and I was lucky, and it all went through. But, I know, and I would say it went through because we did create a great product with great IB. Like ultimately the company had value and that saved at all. But I think of so many moments in time that I made personal mistakes, that really could’ve killed the whole thing.

Dan Li: So, what’s it like that day you wake up and you get the message from PeopleSoft saying that because of this, lease this, we don’t think we can do this deal. Do you call someone, do you make a checklist of things to do next? What’s the process?

Hope Cochran: My method has always been to pursue five avenues at once.

So, I become a bit of a whirling dervish. And I deploy all my resources in all different directions. And I would say that I’ve had to do this on lots of different occasions, whether I’m pursuing raising debt for a large company, I’m going to pursue lots of different avenues. I’m never single thread, anything.

I always have lots of different ways to approach it with the hope that one will come through. The moment of that day, when that happened, I won’t forget it. It’s, we have these moments in our lives that are very memorable, for some people it might be an earthquake or something for me, it’s the day that the lease almost killed my deal.

And yes, I do remember that in all panic. I remember calling lots of advisers reading the legal documents itself. Was there any out I could find? And then ultimately like writing down a message that I could give to my landlord and really going and talking to them and crafting that message really carefully and just hoping I would catch him on a good day. And that’s ultimately what won.

Dan Li: That’s amazing.

Hope Cochran: Yeah.

Dan Li: So, after the startup got acquired by PeopleSoft, instead of sitting back, you went and took another CFO role, cause you wanted to do it again with a company called Evant. How’d you get connected to them. Did you know the team already?

Hope Cochran: I didn’t know the team already. That was a venture capitalist at Kleiner Perkins who reached out to me to come in. And he was really frank about why he was changing out the management team. They had just replaced the CEO and they needed a new CFO. And the company was a ten-year-old startup, meaning that it had been through lots and lots of rounds and recapitalizations, and it had to be reborn.

Basically. And so that’s a very different journey. If you look at my journey and I always say the only consistent theme is a lot of change and a lot of chaos, and that goes in growing and downsizing them. So, I’ve done both sides and that’s what Evant was, and I went into it, eyes open that’s what I would have to do, but I had not done that before.

And when you get in there and you start meeting people and you like them, and you understand how it got to where it is, you gain a lot of sympathy for the process. And I had to look at even the GNA team and realize I had to reduce it by half. I like to be liked. I think we all like to be liked, but that was my job and that was painful.

And it also gave me a different lens on how to grow a company. Meaning growth is fun and good, and you have resources and want to spend it. But if you hire too many people, if your space that you get is too big, it does not lead you down a good path. I tend to know, as a CFO, like crowded offices where everyone’s too busy. Because when you have a crowded office there’s great buzz, people are excited, there’s great energy. And when people are too busy, they don’t have time for politics. So, they don’t worry about their title, or if someone’s doing part of their job. They’re happy for the help. And so, I tend to now approach growth with a different mindset because of the Evant experience.

And yes, I had to make really difficult choices. I think when you have to make those difficult choices about who to keep and who to let go and how to reshape the business, you have to keep in mind that you’re actually helping people’s career. So, look at the talent you have in the organization. They are not being helped by the fact that there’s too many people or that you need to prop up those people that are trying and have talent. And that’s ultimately the benefit of what you’re doing. And just to go back to Skills Village for a moment, one of the things that I did wrong as a young CFO was trying to keep people along for too long. I can coach them; I can train them. When ultimately, if I have a population of 10 people and I have one person that’s not carrying their weight, I’m actually hurting the nine.

So, while I’m avoiding a difficult situation with the one, I’m creating a difficult situation for the nine. So, I have learned in my career to act much faster than I did in those years. And Evant really brought that home to me because I had to make the choices quickly. And when I did, I saw how much healthier the organization was almost right away.

And it was a very painful process, and I would hope to avoid the painful process. But if you have to do it, you are actually benefiting the rest of the organization and yes, you might not be popular, but ultimately, they’re usually grateful.

Dan Li: So, were a lot of the decisions that you had to make at Evant relatively obvious on the key areas, or you had to downsize, or how did you end up coming to all the different decisions that you made there?

Hope Cochran: Yeah, you always think they’re obvious until you start getting to know the situation and then things get complicated because you look, and I guess it is nice to have a little bit of a third-party perspective, because I do think it’s more obvious then, but you can’t then make the changes without really understanding how it came to be.

And, once you understand that you say, oh, this person has this history and this person understands this nuance and that nuance, and it all becomes mucky and hard. And that was clearly the case and you want to be respectful and kind to people as well, so it’s always a very hard process. We did understand that we needed to take the product a different direction, and so that led a lot of the changes, which is always helpful. If you can think in your business, I’m not just downsizing it, but I’m actually refocusing it. I want to get this business objective done, like start with the strategy and figure out how you’re going to get there versus just say, oh, we have to cut costs.

I don’t think that any CFO is ever going to be successful in a, oh, we just have to cut costs, mentality. They really need to think about let’s identify the three or four big objectives this company needs to accomplish. Let’s protect those and make sure that those are shored up and anything that doesn’t directly align with that is what we then need to address in the downsizing.

And that also just enables the message to be a lot better and sets up the company for success.

Dan Li: Makes sense. So then after a lot of that turnaround work was done, what eventually happened to that company?

Hope Cochran: Went through a sales process, which was the intention, and we sold it to another ERP company.

And, in that one, we were just happy that the investors recouped their money because it had been a 10-year journey. But I think, everyone was happy with where it landed.

Dan Li: So now we’re going to get to the really good stuff, billions, and billions of dollars. Apparently Clearwire raised about $9 billion during your tenure.

That’s a lot of money. How do you spend $9 billion?

Hope Cochran: Yeah. So Clearwire was a company that was born out of the premise that someday people would actually use more data over a wireless network than voice. And so that seems to be true today, right? So that was in 2005. And as we look at our usage on our mobile devices, very few of us actually talk on them.

We actually use data. It was a very valid premise. The intention was to take some spectrum that the company owned and make it valuable because it was perfect spectrum for data. Now telecom is an industry that just requires a lot of money. So, in order to make the spectrum valuable, the path to doing that was get it used.

So, in order to get it used, we had to build a network. Building networks are expensive. There’s a reason why there’s only so many big cellular networks in this country today. It’s because it costs billions and billions of dollars to build them. And data networks were even more complex because the towers need to be closer together, so you need more of them. We went back and forth between raising money to build the network, then also raising money to buy more spectrum. So, we basically pulled spectrum together, made it valuable and then built networks on top of it to show its usefulness. And ultimately that company was bought by Sprint for $14 billion.

And is the primary reason, why, or I shouldn’t say the primary reason, but one of the key reasons why the T-Mobile Sprint potential acquisition is being discussed today. Because that particular spectrum is so valuable in regard to being able to roll out these new data networks, specifically 5G.

Dan Li: Got it. And was it quote, unquote obvious in this scenario again, that this would be a bet that played out?

I don’t think that people always had a lot of optimistic views on data versus voice and whether data over the networks was going to be a big thing.

Hope Cochran: I wish more things in business were obvious. I can’t think of anything that’s been obvious. You have to take a leap if it fits all of the right decision criteria.

And I think that is something that we have to think about is we take bets and now on the VC side of the table. How do you decide to invest in a company? You have to be grounded in your own decision process, and remember why you made the decision because we, we try and be analytical, but there’s always two sides to every equation and it’s never obvious.

So no, it wasn’t obvious, but yet all the proof points seem to make sense and seem to indicate that’s where it would lead.

Dan Li: And was there some point, I don’t know, after a billion dollars or $3 billion, where you have a ton of money in the bank, you’ve got customers and contracts, a great team, you think maybe it’s going to be smooth sailing from here?

Hope Cochran: No.

So, we never had billions in the bank. I guess there was like little moments in time when we did, but we would raise several billion every year. And then we would spend that money rolling out a network and we would be getting down to the dribs and drabs and raise another couple billion so we could do it again.

So, it was a constant cycle and that was an eight-year process. And by the end of it, we really were in a situation where we were in the throes of being acquired by multiple different entities. And we had a lot of debt on the balance sheet and if we weren’t acquired, we probably would’ve had to default on that debt.

So, it was a definitely a nail-biting experience, and that’s not uncommon in telecom, I have to say. Telecom is a big game of poker. You have a lot of debt and you basically have to be able to create revenue to then pay off the debt. And in order to do that, build the network. So, it is a high stakes game.

But I had such an amazing crew to work through that with, and I am ever grateful for that team. John Stanton was our leader of the board at that time. Brilliant strategic mind. And so, he led us through that process. So definitely that was such a learning experience for me. And I’ll just say that in all of these situations, whether it’s you’re an operator in a company or a board, the one thing I will say that I have done well is chosen the people around me. Your reputation is never your own. I would love to say that these successes have been mine, but they haven’t. They’ve been the people sitting at the table with me. You never make a decision in a vacuum. You are influenced by all those around you.

And in every situation, I’ve been in, there have been moments that have been very stressful, there have been moments where people’s personal issues have come out, whether it be financial or home life or whatnot. And you really get down to the core of who the individuals are and how they make decisions in that time influences how the company will move forward, how your career will move forward. And I have been so fortunate to be surrounded by high integrity, fabulous people, and all of these situations that I feel like as my failings came out, they were there to catch me. And as their failings came out, I caught them. And I really think that has been a key to my whole journey.

Dan Li: That’s awesome. So, at Clearwire what was that 4:00 AM phone call that corresponds to the landlord or the downsize, or the announcement?

Hope Cochran: There was many, but I remember one specifically and it’s quite technical, but it was the day SoftBank announced that they were buying Sprint.

And the reason why that was important is I was at a big conference and I was speaking all day. I think I had 14 investor calls lined up that day, as well as a big public speech. And the reason why SoftBank was buying Sprint is because, while I’m sure they were excited about the U S telecom, but they also wanted this asset that Clearwire held because Sprint owned a portion of that asset through an ownership percentage of Clearwire. And so, all of the sudden it was exactly 4:00 AM, my phone started ringing off the hook and everyone wanted my opinion on this particular acquisition and our stock I think tripled at the opening. Because everyone felt it had big implications for me and I was in a very public situation with every investor and all eyes on me.

Dan Li: So, you have a day of investor meetings lined up, and these 4:00 AM calls are asking you what’s going to happen.

Hope Cochran: And to be fair, I knew SoftBank, but I didn’t know them all that well. So, I basically spent an hour cramming on all SoftBank related items.

And knowing that any word I said would end up in lawsuits if it was incorrect, so I had to be incredibly accurate with my words. I was on the phone with lawyers all morning so that I wouldn’t miss step. And we went through about three hours’ worth of meetings in the morning and the stock continued to run and we, ultimately made the decisions, the lawyers made the decisions that I needed to leave the building. So, I did leave the building because I was too surrounded by investors and the liability of what was happening with the stock was too strong. So, we got up and walked out and it was like my little moment of rockstar in a little tiny world.

Like no one really cares but we cared. And we walked out and ultimately that was the beginning of what led to SoftBank buying Sprint, and Sprint then buying Clearwire, because SoftBank didn’t need the asset we had. Now that was another year and a half down the road because it took that long, but that was the thing that kickstarted the process.

Dan Li: What a cool story. How did the eventual acquisition play out and then what did you decide after that?

Hope Cochran: How the acquisition played out is a very long and complicated question of which I think we would bore the world with, but it was a very curvy road. It was on and off and there were other players that came in and tried to acquire the entity. Ultimately it was purchased in 2013 in the spring. And, as a CFO, especially when you’re a public company, CFO, it’s pretty common that that’s the end of the public company CFOs journey with that entity.

So that is when I then decided to take a role in London with King Digital, and we moved the family over to London and I was the CFO of King Digital for my next adventure. And, King Digital makes the game Candy Crush, for those who might not know. But many people know Candy Crush. In fact, 500 million people play Candy Crush every month.

Dan Li: And what level are you on?

Hope Cochran: I don’t even know, I’m basically right at the end. They come out with 15 levels every week. So, you have to really stay on it.

Dan Li: There’s like a huge proportion of the user base, that’s on that last level, right?

Hope Cochran: There is, yes. And one of the things that we love to talk about at King is that 50% get there without paying anything.

Dan Li: Wow.

Hope Cochran: I know. I don’t know how they do that. I admit that’s not me.

Dan Li: So, the way I understand the King story, it’s a company that’s doing really well for several years, making tens of millions of dollars and then one day, boom, Candy Crush. Huge phenomenon, like what we’re seeing today with a Fortnight, and just overnight success, everyone’s talking about it, everyone’s ecstatic, we read about it everywhere, everyone’s playing it. Is that what it felt like on the company side?

Hope Cochran: It did. It really did. So, for 10 years and it was the 10 years I wasn’t there, it was making about 60 million in revenue based on smaller games.

And then one of my favorite stories from them was that over Christmas break, they were getting in their daily reports from the network. And they basically didn’t believe the numbers because the numbers were too big. So, they just ignored them. And they came back in January to really do a deep dive, to understand what was happening with their analytics.

And they realized they were accurate, and Candy Crush had taken off. The company went from 60 million in revenue for a year to 2.4 billion in revenue the year after due to Candy Crush. And approximately 800 million of that was cash to the company. Huge cash generated. They basically saw that they had an opportunity here and they wanted to get the company public.

And that’s when I joined on, when I joined on, as the CFO, they had already filed their documents to go public. So, I was coming in when it was already underway and had to get the company ready in about three months to then enter the public markets.

Dan Li: So that’s probably like a slow lethargic process with lots of controls.

What were those three months like?

Hope Cochran: The thing, the first thing I learned and again, I’d put this in the failing’s category, because I probably should’ve learned this before I joined, was that hiring in Europe is not a quick process.

Dan Li: So, actually it wasn’t a quick process.

Hope Cochran: Yeah. It was not a quick process. And I had a very light finance team if we can call it that. So here I was about to take your company public. I really had no team. I had no staff and what I realized in Europe is anyone that takes a job has to give three months of notice to its prior job or six months. And I was taking this company public and three months, so that was not going to work. So, the good news is I had just sold a great company in Seattle, Washington, Clearwire to Sprint. And I basically called everyone that worked for me, and I said, please move to Europe tomorrow and do this with me again. And so, I was very fortunate to have fabulous, talented people who like jumped on planes and came over and together we joined hands and got this company ready for the public markets.

Dan Li: Wow. In those three months, what were some of the things that had like the longest skating times or the toughest to get across the line?

Hope Cochran: Yeah, there were everything from like building the company’s financial models, which they didn’t really, have to figuring out the data analytics because the data analytics had never had any structure to them before, so they had been pulled, differently for every month for the past few years, and I needed consistent data if you’re going to go out publicly. So, I had to rework the data analytics and then, too, we were incorporated in Malta and you can’t bring a Maltese company public in New York. That’s just not going to fly, so I had to reincorporate it into Ireland. And that just takes time.

Dan Li: That’s so cool. This sounds like one of these times we’ve talked about this acronym a few times, FTJ that you use with your kids, and that stands for finish the job. This sounds like one of those times you could have started making FTJ your motto but tell us about that. How’d that come into play?

Hope Cochran: So FTJ is something I learned as a high school camper. So, I’ve been very involved with Young Life, my whole life. And I worked at their camps over the summers, and you get exhausted and tired. And I remember one of my leaders always using this phrase FTJ, which was, you don’t get any credit for something if you do a really good job, but then you actually don’t finish it. And I think this pertains to so much in our careers. Meaning, you could do a ton of research on a topic, but if you don’t produce the document in a professional way, for someone to read, they discount the work that you did. So, you need to spend that extra energy at that moment when you’re tired to complete it in a professional way that you would be proud of.

And that’s where I say FTJ, last night my children were doing laundry and they washed and dried the clothes but didn’t fold them. I don’t give them any credit for doing the laundry. that’s not FTJ, right? Like it, it just pertains to every little moment in life. Yes. Taking King public was clearly a big FTJ moment, but that one was like really big.

I actually think it’s more pertinent on the little everyday things in life where you just get things done and you finish them, and you finish them. In a way that makes you proud that you produced a positive and professional outcome.

Dan Li: That makes sense. Speaking of kids, one of the topics I do want to bring up here is having kids and starting a family.

Fortunately, and unfortunately, a lot of career growth happens at the same time that people are thinking about having kids. How do you generally think about this balance of spending time with your companies, the management teams and the board members versus your kids and your family?

Hope Cochran: I always muse about this.

We have, what, 90 years on this earth, I don’t know what the average life expectancy is. And really 20 of them, are killer, meaning that they’re the 20, when your job is taking off and you’re having your kids, they all happen in your late twenties, thirties, forties, and there’s this crux of everything comes down at you at once.

And so how do you manage through those years? I think number one, recognizing that it doesn’t have to be a straight line, is important. And number two, having a few little rules that can help you get through there. Like I would say in general, yes. I have had a very busy career. I also have three children that I want to parent well and do all the right things by. Probably my social life has not flourished as a result of all of that, meaning I’m not going out at night.

And so, you just make choices, you make choices about where you spend your time. I’m also very big on, I don’t try and strive for this balanced life that people talk about being balanced. I think, I don’t know a single soul that would say, Oh, I feel so balanced today. Whether they have kids or don’t have kids, that’s, what does that even mean?

So, I really look for what I consider an integrated life. Meaning, what do I have to get done today and how am I going to get that done? And it might be that, yesterday I took my fifth grader to look at a new school. And so, from 11 to one, that’s where I was, and I cleared my calendar. So that could happen. That was the priority of that moment. So, as I look at each day, I look at it individually. And how do I prioritize my days such that it is in line with, I want to say my objectives, but the things that are important to me.

Dan Li: So, on this topic of the moments of truth and the 4:00 AM phone calls and the doubt, did you ever have doubts about how you were prioritizing time at work versus time with your family?

Hope Cochran: I think every parent has doubts. It never feels like you can give enough. And that’s just part of the journey. I wish there were a good answer to that. I think you’re always going to doubt. The one thing I will say though, is I do feel that for the times that I was away because I was on work trips or whatnot, my kids know that I am their mother and that I love them. And if there’s something they need, they call me, they don’t call a nanny. They don’t call my husband. They call me like that role as a mother is never removed. And that has been comforting to me over the years. Cause I think when they were little and I didn’t have that perspective, I worried that, they turned to someone else because I wasn’t there when they had a nightmare and, no, that’s never happened.

I am very close to all of my kids and, you never say your journey as a parent is over. So, I don’t know if I’ve done enough, but you have to give yourself a little forgiveness.

Dan Li: Yeah. So, let’s talk a little bit more about what you’re working on today. We spend a bunch of time together at Madrona looking at companies and sometime in the gaming world and the FinTech world. Obviously, you’ve done a lot of stuff in those industries, but these days you’re in the investor seat, advising lots of founders and early-stage companies and company building. And I think the thing that we hear a lot today, and people like to tell potential founders is this, yes, go start a company, dropout of school, leave that job at Microsoft. What’s the worst that can happen? It’ll be a great learning experience, no matter what. Do you agree with that advice?

Hope Cochran: That’s an excellent question. I’ll first say that I love working with young companies and I love joining the entrepreneurs on this journey. I feel like they’re so courageous.

It takes a lot of courage to jump on this train and try and build your own company. So, everyone that I meet with, I walk in with humility and humbleness, and just want to be helpful to them in terms of leaving colleges. I don’t know. I think everyone has to have their own journey, leaving schools or pursuing something.

I do think there is no cookie cutter approach. I think every journey is unique. If I were to have one word of advice for my children. So that’s always where it comes down to the rubber meets the road. I probably would like them to finish school.

Dan Li: And which school is college or high school?

Hope Cochran: I have ambitions for them for college. But would I be open to listening to why they want to take a different fork in the road? Of course. So, I do think that in today’s day and age, there’s lots of ways to approach this. Back to what we were saying earlier, where like the crux of busy-ness happens in these twenties, thirties, and forties. That road doesn’t need to be that straight either. There’s different paths and thing. We need to create a work life that fits different lifestyles and journeys. And this is in that vein.

Dan Li: And going back to FTJ and finishing the job, you’ve been at a bunch of companies where the job has been finished, whether it’s an IPO or an acquisition from this side of the table, what do you see as the most common reason that startups or entrepreneurs end up failing?

Hope Cochran: Clearly, assuming, they have gone on a journey where the product is a good fit. So, we’re going to put that aside cause we’re, you don’t start a company if you don’t think there’s a good place in the market for what you’re building. So, let’s assume that’s happened. The number one reason, I see things fail is people. And what I mean by that is relationships, dynamics. I think the founder dynamic, or the co-founder dynamic is so hard. And people should never underestimate that. I definitely felt that my co-founder and I did really well together, but when you are embarking on a journey to start a company, Life happens.

Meaning are you both at the same financial place where you can put in this, financial resources or take lower salaries? What are your needs at home? Do you need to be home more than your co-founder? All of these things become very stressful and very important to work through. I would also say that just having the ability to emotionally support each other.

So, starting a company is really hard. And I don’t think people understand that unless they’ve done it and being able to be support crew for each other when one is feeling down, and the other one can help each other. I think this relationship is so important as companies are getting off the ground.

Dan Li: Yeah. And you’ve talked about this, the support network and the people and advisors around you that are helping you make decisions, and you have a great network of CFOs that you rely on and organize events for. How do you go about building that if you’re still earlier on in your career or just getting started with your startup?

Hope Cochran: Yeah. I don’t know that I ever had any formula. Like I said, I didn’t have a lot of extra time, so I wasn’t good at going to events or networking. I think it was really just about making sure that the people I was choosing to partner with were people that I wouldn’t mind raising my children. Meaning, I had to really love them and make sure that our values aligned and that the level of integrity was there because you do end up in really difficult, stressful times with these people and you have to be able to ride that journey together.

Dan Li: What’s your least favorite part of the job at Madrona? And then we’ll do most favorite part afterwards.

Hope Cochran: Yes. My least favorite part is really clear. And that is, I always say I was really fortunate, I married my high school sweetheart, and that’s still working out, so I’m good.

Like I haven’t had to break up with people. It’s not a skill that I have or that I’m comfortable with. And I think that reality of venture capital is you meet so many companies. And as I was talking about before, like I find these entrepreneurs so brave and courageous, and I just love their desire to embark on this journey.

And I just hate how many no’s I have to say. And often I’m saying no, not because it’s a bad idea or because I don’t believe in them, but for whatever reason, it doesn’t fit the Madrona structure, or maybe it shouldn’t be backed by VC. It should be backed in a different way. And so, I always find myself like wanting to then help them.

And I get myself completely overscheduled because I ended up helping all these companies, but I’m really awful at breaking up.

Dan Li: And then what’s the, what’s your favorite part of the job? I’m guessing it’s going to be related.

Hope Cochran: My favorite part of the job is finding that company and digging in with them and helping them build something. That’s what I love doing.

Dan Li: Yeah, definitely the best part of this job.

Hope Cochran: Absolutely.

Dan Li: This has been such a fun interview. I love hearing all these stories. So, one last question for you. If you were someone five to 10 years out of school today, interested in the tech and startup world, asking for a friend, what would you do?

Hope Cochran: I would, I, one of the things that my career lent itself to, which I didn’t really contemplate at the beginning, but has really done me in good stead is I’ve gone from tiny companies to big companies, to tiny companies, to big companies. And that actually has been incredibly useful. So, I clearly love starting things and building them, but also seeing how that plays out in a healthy big environment helped me build things in a healthy way. And so, having that perspective of being in a big company, like a Deloitte and Touche, which sounds really boring, but actually I learned great skills and then going to a little startup, and then going into PeopleSoft where it was 5,000 people and it was led in a really effective way.

And then I went and started my own company and I thought, I really like how they did this and I’m going to build it to that. I had a vision of where I was going to go. So, I think getting those different experiences and seeing all different environments is really important. You can learn a lot from a company with a great culture, and you can learn a lot from a company with a bad culture.

You can learn a lot from a great manager, and you can learn even more from a bad manager. Your career is your own. It doesn’t matter if you have a good manager or a bad manager, you’re in a bad culture. A good culture is to take those learnings and then apply them to whatever you’re wanting to build.

Dan Li: That’s awesome. Thanks Hope. Really enjoyed this podcast.