The 5 Best Pieces of Advice I Ever Got From My Mentors

To do a deep dive on the five best pieces of advice in my entire career that I have gotten from my mentors. And mentors are so important, and they're important at all stages. And I don't mean a thousand random advisors. I don't need people who, who want to help a little bit. I don't mean investors that when you send the email out, they respond, go, Jason or great month. I mean great. A bunch of those are nice and once in a while they'll make an introduction or help a little. No, I'm talking about at each phase. And the phase you are at will change every four to five years as founders, as CEO, one or two folks that have literally done it before, that are invested in you, that a couple times that will keep close enough tabs on you, that a couple times a year, when you have big decisions to make, big issues, big things to grapple with, they could really help you. We all need those. I've needed those. When I've looked back on the biggest mistakes I've made as a founder, it's usually not having the right mentor, the right person to help me think through the tough decisions. So, okay, so of all the years, what are the five best pieces of advice I have the number one piece of advice I got. I remember back in the day, the early days of Adobe Sign, Echo Sign, when I was CEO and we were going to fail, we were going to run out of money. We were not growing quick enough. My co founder had walked out the door. My CTO was angry at me. With hindsight, we weren't doing as badly as I thought. Had hundreds of happy paying customers, but the product really wasn't there and we were going to run out of money and I just did not know what to do. And I went to my old boss, Mark Selko, who is now a general partner at Cosa Noa Ventures. But he had been my first Internet boss. And I went to Mark and I said, what to do? And he kind of, and he's one of the nicest, most generous people, and he kind of gave me a scowl. He's like, well, how many of your, how many of your customers and prospects have you visited in person this month? And I said, none. I'm sitting in front of the computer typing on the keyboard, waiting for leads to come in. And he just shook his head. I wouldn't say it was with disdain because he's a great, positive person, but it was with disappointment. He's like, you got to go visit your customers. And it was an Aha moment for me. And I got out there and I visited all the top customers and just talked to them. It's more important. We do a lot of this when things are going great, we do a little victory lap and we go meet with our big customers because we're supposed to do it. And we take them out to lunch or do whatever you do. But no, this is more important in tougher times. Your existing customers, if they've renewed, if they're using your product, if they're active, they're highly engaged, they are thinking about the problems you're solving, they know your feature gaps, not all of them, but they know the ones that matter to you and they know the things, at least from their perspective. And if you could just get that done, if you could just get there, it would be a game changer. And my old boss and mentor was right. And I went out and did that and met with all of our top customers, the bts, the ges, the Comcast and others. And I just learned so much. I learned, really, it was a kick in the arse to go out and build some of the core gaps that we still had. And it worked. It worked. And I give this advice again and again. And I see way too many founders, when times are tough, retreat. I see this nine times out of ten, they hide, they don't get out and visit customers. They, they retreat, they cut the burn. Maybe they'll do a layoff or two and they'll settle for mediocre growth or even no growth. But I ask founders that are going through tough times, I asked what my old mentor told me, how many of your customers have visited this month? And too often I hear zero. Too often, you're not going to learn anything staring at your keyboard, you're not going to learn anything hoping you're not going to learn anything building features that might or might not work, but you will always come back from your top customers inspired, maybe beat up a little bit, but inspired with where to take the company. So that was the best advice when you, when you don't know what to do, go visit your customers. It always works on so many levels. Point number two, and I still struggle with this today, but you'll see so many VCs say this, and it took me a while to get it, but you've got to become a tenacious recruiter. I see so many founders stall out somewhere between 4, 5, 6 million ARR, and then again maybe at 10 to 15 to 20, and again after that, if they are not tenacious, recruiters and what I mean is, look, you can't get anywhere as founders if you're, if you're not a decent, like, sequential recruiter. Like, you got to find a good co founder and then you got to find a good sales rep and then a good marketer and a good VP of sales and a good VP of product and VP of engine. But a lot of us are really sequential recruiters. When we have a desperate need, we kind of drop some things and we go out and we hire one person. Frankly, I still have those weaknesses today. But the best CEOs and founders are constantly recruiting at all times. They are spending, literally spending 20 to 30% of their time recruiting every week. They are doing at least 10 interviews a week. Every week. You've got to spend 20 to 30% of your time. And I say this, a lot of founders nod the head and then I'm like, be honest. Have you really spent 20% of your time recruiting this weekend? And the truth is, most founders will do one or two interviews a week max, and they are not spending 20% of their time. They are not spending 10 or more hours recruiting. And sure, there's no point in interviewing some Brando that applies off LinkedIn, that can't even write a cover letter or write a single word about what your company does. I'm not suggesting you do that. I'm suggesting you go the extra yard. I'm suggesting that you remind yourself that you're probably going to have to interview 30 qualified candidates to find a great VP. Where are you going to find those 30? Where are you going to find those thirty? Sitting, sitting again in front of your keyboard, waiting for them to come in. No, you've got to do more. You've got to find a new recruiter. You've got to find a new path. You've got to reach out. You've got to do more. Whatever it is, challenge yourself. Take a look at your schedule. Did you spend 20% of your time truly recruiting this week? There's no way you did. And too many founders fall into this hole and they do it themselves, themselves. They stay the VP of Sales themselves too long. They do product themselves too long. And no, even as early as 1 or 2 million in ARR. If you have the capital, if you do and you're growing, you're ready for a VP of everything. You're ready to not do it yourself. Things are starting to get complicated. Do you have 50 hours a week to be the VP of Sales? Do you have 50 hours a week to be the VP of Product. No you don't. Once any function becomes a 50 hour a week function, you need ahead of it and go hire them. So become a tenacious recruiter. All wherever they came from. Even if they were an individual, individual contributor engineer that never knew how to do sales, they become tenacious recruiters to great ones. They figure out how to hire a great VP of sales. And you'll see this at a most extreme level. Forget about founders, you'll see this and I've written about this so many times, you'll see this at the most extreme level with great VPs of sales. Because sales is this human capital industry. You have to constantly be hiring to hit the number there. There are no economies of scale. So any good VP of sales is a tenacious recruiter. That's why they always have three or four people that will follow them. That's why they always have a whole network of folks draw on because it's impossible to do the job well if you're not a tenacious recruiter. So learn from VPs of sales that you know, how did they do it? How do they constantly recruit? What are they doing? Copy their playbook. But you need to become one. One or another. Become a tenacious recruiter. That's the number two thing I learned from my mentors. I'm still struggling with it to this day, but I think about it every single day. How can I become a more tenacious recruiter? The third one, this was some advice I got very early on from an old boss and, and I'm struggling to rethink it in today's world. But it's don't let the good ones go. Don't let the good ones go. And the world has changed. The world has changed. It used to be it was mainly pirates and romantics and startups. It used to be only startup peoples did. Startups used to be had to be a little bit kooky, maybe even a little bit weird to join startups. Now startups are very mainstream and it's changed everything. It's changed how long people want to stay in roles. It's changed how they approach roles. With startups it's changed expectations, turnovers, higher voluntary attritions higher side hustles are everywhere. But you, you still got to make sure the great ones don't let them go. Never. Never. And I love it. And what this means is a couple of things. Your, your startup's going to change as, as you know everyone talks about and writes about you won't be the same at 10 million ARR as you were at 1 and you won't be the same at 30 as you were at 10 and 100 at 30. Of course that's true. And one way you can look at it is, hey, I've got to, I've got to constantly be hiring new people. And you do, you do. If you're lucky, if you're lucky, half your VPs can scale from one phase to another, can fit that one transition to another. And that, that is why there is a lot of transition at the vp level over 24 months. But you don't want that. You want to keep them. So look, if they're good, find a place for them. And one of the classic mistakes you see all the time is a company hits a certain phase and that great first VP of sales is not, it's not clear. They can be the CRO at 100 million, 200 million ARR. And the founders bring in some CRO and that, that first VP of Sales leaves. No, that's a tragedy. That's a tragedy if that person is the one that got you from nothing to million as your head of sales. Keep them whatever it takes. If you need to change their role, if they need to be VP of Commercial sales, which is a common way to do it, you take that existing VP of sales and you have them handle the smaller customers that sometimes the CRO doesn't want to do. That's a classic way to do it. A VP of something, even an SVP of something. I never see it work out well when some fancy CRO comes in and that great first VP of sales departs quickly. No, that's the most extreme example. Never let them go. Yes. Do you have to top people? And I know that, that that term can almost be triggering. Do you have to level people and hire folks above people? Yeah. At least half your VPs are going to need to be top. But that doesn't need. Here's the key insight. It doesn't mean their role needs to be shrunk. If you've got a great person, that's your first head of product and you bring in this chief Product officer. I mean heck, 90 of the chief Product officers I know are not hands on. Most of them don't even visit customers. It's a tragedy. Find that first head of product and make them VP of like new products, VP of integrations, VP of something. Don't let that, all that expertise, that passion, that knowledge go out the door. Whatever you do, don't. Don't let the good ones go. And this is for managers as you scale, but it's also for ICs. And the original time I got this, I remember when we were, when we were scaling one of my best engineers, I could see him on, on, on his mobile phone in the driveway. And I knew that was strange. And I went out and I chatted, you know, you're not thinking of going, are you? And he's like, yeah, I have this offer. I'm like, okay, I screwed up. I'm sorry. I love you. You are so important here. What can I do? And in that case, all it took was a small raise. It's embarrassing. I did not know that all it took was telling them that I love them, that I wanted them to stay in a small race to get them. But whatever it does, do not let the good ones go. And again, I see this happen in phase transitions all the time. I don't know how to fit Lauren or Bob or Bill or Jane into my organization anymore. I don't know. And they leave, maybe. But I see so many folks now in the most successful SaaS companies with that first head of sales, head of product, that first marketer being there five, six, eight years down the road, that domain expertise, that, that knowledge of the core customer, that passion, that ability to understand the core customer. You often don't get it with the later people. So don't let the good ones go. Okay, point four is really a meta point on what we've been talking about, but go find that great mentor. Go find out. Ask yourself, do you really have this person? Do you have someone you can talk to about two to three decisions a quarter? For real? Not someone that's going to give you platitudes, not someone that worked somewhere fancy per se. That's not enough. But the one to talk to about the two or three things that matter. Should I invest my limited capital there? Should I make this risky hire? Should I sell my company? Should I raise the round? Should I partner with someone that might compete with me? I just got to tell you, there's just so much terrible advice out there. There's so much advice from VCs that haven't done it. There's so much dated advice, there's so much biased advice. There's so much Internet and LinkedIn advice and soak it up. Because, you know, almost all of this advice from someone that's experienced has germs of truth in it. But goodness, you can be overwhelmed in the mediocrity of advice today, with so many veterans and so many VCs out there, find one or two people that you can ask these tough questions to. And sometimes the answers are tough, sometimes these folks are, are more abrasive. And oftentimes these folks, they, they don't. You know, you've got to seek them out, you've got to ask them because you probably can't pay them enough to help you. You probably can't motivate. They have to want to do it. But whatever it does, be a heat seeking missile and find one or two great mentors that you can work on. The couple tough decisions a year. And again, I said this at the beginning. This made the biggest mistakes in my career. I have made three or four terrible mistakes, often in transition moments. And I have talked to people about all of them. I've talked to multiple people, but I haven't. I've lacked the right mentor and come to the wrong conclusions. And this is coming from someone for Saster that has given thousands of pieces of advice, most of which I think is correct, almost all of it, which I think has a lot of truth in it. But every situation is different. And when I look back on my biggest errors, my biggest mistakes, they were when the choice wasn't clear, when both were tough choices, or when both were good choices. The mistakes I made. If I just had that one great mentor to provide me that magical insight. Jason, here's why you should do this or shouldn't do this. The upside could have been insane, folks. Okay, the last point in this one, this one took me a while to figure out. Maybe you've already figured it out, but it took me some life experience. You'll probably get another chance if you go long. In everything. In everything I remember. I'll give you an example. Back in the early days of E Signatures, we were one of the. We were the number one highest rated app on the Salesforce App Exchange in the early days of AppExchange. The early days. But we did not have a deep relationship with Salesforce. And I remember when Salesforce told us that they were going to partner with DocuSign despite us having 10 times more customers at the time on the partner, despite us having a thousand five star reviews, they were going to partner with DocuSign. And the specific reason was very interesting, which was that the CEO was very close to the CRO at the time, which is a reminder of the power of those high level relationships sometimes. But that's not really the point. The point was it was, it was a tough blow. We had 10 or 20% of our customer base came from Salesforce and to Think all of a sudden the game was no longer going to be equal. That we were. That we were going to be competing with our partner, that they were going to recommend DocuSign over us was a huge body blow that maybe in some ways led to us deciding to sell. But you know what? And it was a real blow. And they really did recommend us, and it really did hurt us. But you know what? It didn't really stop anything after that happened. We still closed Facebook, we closed Google, we closed Yelp, we closed Twitter. Okay? And this is just one example of, you're probably going to get another chance if you go long. You're going to get another bite at the apple. There are some decisions that it can't be fixed. There are some mistakes that are so big, that are so big, you really should call it a day. You should throw in the towel. But boy, a great set of founders committed to a space with a group of happy customers. You'll get another shot at something. And even if you don't, the world changes every couple of years. A great partner today may be on the outs down the road. You know, you just don't know. But you'll get another chance. The market will change and great folks will take advantage of it. And so, yes, when those body blows come, when those tough times come, take it seriously. But boy, go long enough and everyone gets another chance. My friends, those are my top five pieces of advice. When you don't know what to do, go visit your customers to become a tenacious recruiter. Yes, it's hard. Yes, I'm not even great at it. Find a way. Three, don't let your good ones go. Find them a spot. Four, find a great mentor for the tough decisions. And five, I learned this one again and again, too. You'll get another chance if you go long. We all get three, four, five, six chances at all this. We don't get 100. But if you're really committed, if you want to be in tech, if you've got the right vision, you'll. You'll get another shot at just about everything.