The 7 Best Pieces of Startup Business Advice I've Ever Been Given

Hey, everybody. I wanted to share the top seven pieces of business advice I was ever given in my whole career. Reflecting back, and then I thought I would add a few bonus ones that maybe weren't the best piece of advice, but actually at given at certain moments in time, were the most impactful. So what are the best pieces of business advice I was given so maybe I can share back to you to think about to make it just a little bit easier for you to get up that hill, for you to get to five, ten, twenty, fifty, a hundred million in ARR. Okay, so number one, especially this is more geared to folks earlier in their career and who aren't founders yet. Probably the best bit of advice I ever got from a boss was manage people and do it earlier. There was a time in my first startup job where I was a great IC. I was one of those 10x employees. I got everything done faster. I did more, I raised my hand, I had more on my plate, but I liked that and I liked reporting to the CEO. That was what I wanted to do. The last thing I wanted to do was get into management. But the president of the startup came to me and I said, they said, we need help, Jason. We want you to manage the HR department. And I, I didn't roll my eyes. I might today. I was a little bit younger then, but I said, respectfully, thank you, but no, I, I don't really want to be a director of HR or chief people officer someday. The last thing I want to do is manage hr. I want to do more deals, I want to do more sales, more business development, that sort of stuff. And my, my president said, okay, that's fine, I understand. But he turned to me and said, listen, I've been doing this a little bit longer. You need management experience. This is what I learned as a young executive at a top tech company. So think on it and let me know tomorrow if you still don't want to do it. And I thought on it that night, and actually, I wasn't sure it was right. I wasn't sure that just because he'd worked at a big tech company as a young manager, young director of product, that was the right path for me. But I knew he knew more than me. So I, I came in tomorrow, said, yes, I'll take it. I'll manage that HR team of four people. And it was the start of learning how to be a manager. I'm not sure I'm a great manager today, but at least I know the toolkit pretty well. I know how to hire. I know how to fire, I know how to spot issues, I know the processes. And to build anything as a startup in tech, you're going to have to do more than just find a co founder. You're going to have to build a team. If earlier in your career you can really manage people. This doesn't mean be a strategist, it doesn't mean tell everybody what to do, but it does mean learn how to manage people earlier. Okay, number two, and this is a subtle one, but boy, it's impactful, which is listen to audibles and act on them. And another one of my bosses said to me, said this to me early on. At first I didn't know what he meant, but we were at a super important pitch, a super important pitch. And I was a young executive together with my CEO and I was standing up there, I was pretty good. I had the passion, I had the energy for the product, but. But said something really wrong in the pitch. It was wrong technically, it was something maybe I should have understood, but I didn't. And my co literally passed me a note across the table and I picked it up and it gave me the right answer and I quickly course corrected it and got it. And that meeting ended up being very successful. And I've since seen this happen in so many situations, intense situations, in pitches, in sales pitches. When you're pitching VCs, which is have a no look pass team where you can listen to audibles and have a situation of trust where you can act on these in real time, where you can leverage it in real time if someone else, simply put, if someone else great is in the room with you. These audibles can make the difference between a positive outcome and a negative one. And I remember on the flip side, in the early days of Adobe Sign and Echo Sign, I was at a critical meeting. We were at a top 10 tech company and it was a favor. It was a favor. They were going to give us a deal. Uh, I knew an SVP there and he said, listen, well, I know it's early, but it'll really help you a lot. I'll let you do a deal. And we had to do a big pitch to about 30 people on the IT team and. But it was complicated. There was a lot to understand, there were a lot to understand with integrations with things that I didn't understand. Different types of LDAP and single sign on and others, they were just beyond my expertise. But luckily my co founder was going to be there, who was a, who was a product guru but didn't show up to the meeting, didn't show up to the meeting. And I did my best, but it wasn't enough. I didn't have those audibles. I didn't have that help. And we went from closing a Top Logo account to losing it forever. Losing it to our top competitor for over a decade. Okay, point number three or piece of advice number three, best piece of advice I was given. And you'll hear this from so many people. You'll see it all over social media today from the best leaders, but it's still so important. Celebrate your wins. This is tough for us to do as founders because there's always another quarter. Hooray. It's the last day of the month that we had a great month, but the rest of the quarter looks harder. Next month is trickier. We pulled in a lot of deals or, yeah, great, we hit the plan for this year. Next year we've got to double again. And as founders, we often, at best, pretend to celebrate the wins or we forget them or we go out for a drink and come back and work at our desk again. And I get it. And look, as founders, maybe you don't actually need to celebrate the wins. Maybe you don't feel it, but the team does. The team needs to feel that it's a big part of the reason we do it. We do it for the team, for the friendships, for the relationships. I saw a tweet the other day by a great sales executive saying, why do sales teams stay together? And you think it's for the money or for the leadership, and leadership's a big piece, but he made an interesting point. It's for the friendships. I'm still staying at this mature SaaS company now for eight years because of all my friends. And you got to celebrate those wins together. So force yourself to. Don't celebrate fake victories. That's something founders struggle with. We were supposed to grow a hundred percent this year. We grew 8%. Hooray. We grew. Maybe if that's. You can celebrate fake victories. I don't think most of us are good at that. But if you do have a win, even a small one, Celebrate, folks. Celebrate. It means a lot to the team. Okay, point number four. I think I've written this 800 times on Saster, but I can't. I can't write it enough, because this is the number one failing that I see with founders. Number one failing with myself as well. Spend 20% of your time recruiting, period. Nothing else matters after the early days. Sure, in the very early days, when it's you or two or three co founders and you're just coding and making a few calls. Recruiting's onboarding. It was important because you got your founding team together, but it's all you need for a while. Sometimes it's all you need for a year or two if, if it's very early. But after that, nothing's more important important than getting the best on your team. And none of us spend enough time. I literally the other day I just had lunch with two of the best founders I know coming up on 40 million. But they were struggling. They were struggling. They didn't have enough good VPs on the team. And I just, I asked honestly, how much do you spend 20% of your time recruiting to the CEO? He said, Sometimes when I'm in recruiting mode, it's not enough. It's not enough. When you talk to the best CEOs at scale, they are spending at least 20% of their time recruiting all the time. They're constantly meeting candidates. The only way to do it, it's the only way to do it. The only way to do it is to meet 20 to 30 great candidates per position. And the only way you're really going to meet 20 or 30 great candidates per position is if you force yourself to spend 20% of your time recruiting.5. I've also said this probably 300, 400, 800 times on saster.com but go visit your customers in person. Go, go visit your customers in person. This was a great piece of advice I got from one of my old bosses in the early days. I did it in my first startup because we were very enterprise. We only had seven figure customers, so you gotta show up. I never thought otherwise. There were only a handful of customers. They were all seven figure deals. It was all do or die. It was all whale. My co founder and I. Every six weeks we would show up and visit our customers. In fact, we came so often, sometimes our customers didn't even want to see us. There was nothing new to talk about. So my first startup was enterprise. So I was there all the time. But the second time when it was more high volume in SaaS, I didn't, I rarely visited a customer. And I remember when things were tough in the early days, we had maybe 10, 20, 30k in Mr. But it wasn't enough and the growth wasn't fast enough. I went with, went to meet with one of my first bosses and I, I talked about the struggles and, and the issues we were having. He said, how many of your, how many of your customers? And Prospects. Have you visited? And I said honestly, none of this one. They're all small deals. These aren't million dollar deals. These are 2k deals, 3k deal, 5k deals. I, I, I shouldn't be going to visit them. Is you. You won't get yourself out of this hole until you go visit them. It's profound. And he's right. Go visit your customers as often as you can. If nothing else, make sure someone is meeting your biggest customers twice a year. Do a customer conference as early as you can. And even if you don't do a conference, just do dinners, do everything. Make sure you are meeting your biggest customers twice a year. And make sure as you staff up a CS team that they're meeting as many customers as humanly possible several times a year. And make sure you try to do 8 to 10 customer zooms per week if you can as founders. 8 to 10 per week. Most of us don't do enough. Now zoom is not a substitute for a customer visit as we talked about in that first story, but it's a heck of a lot better than nothing. So see if you can do four customer visits a month and eight to 10 customer zooms a week. It's a lot, but it will change the direction of your company. But net you're not visiting enough customers in person. I know you're not. Point six I'm not the first to have said this. So many leaders say this, but it's advice I can't give enough and it's mistake again that I've made so many times as a founder. Slow down the biggest decisions, speed up all the other ones. Slow down the biggest decisions, speed up all the other ones. So much great advice in that it almost sounds trite. It almost sounds like a silly thing that was made up in some 50s executive management handbook at some big company. But it's not. Why is this so important? Why slow down the big decisions and speed up the other ones? It's because as founders, it's, it's just first of all, we're too small. There's too much to do and we are overwhelmed with decisions, many of which seem so important. Many of which are important. But the biggest mistakes I've made are making big decisions too quickly and slowing down other ones. Big decisions too quickly. Selling your company make don't make that decision too quickly. Hiring an executive when you're not sure. When you're not sure. Hiring a VP of engineering, a VP of sales, a VP of Marketing if you think they're the right one. But you're not sure. Have them talk to another person you trust. Spend more time with them. Do one more when your gut's not sure, raising from the wrong investors. Whatever it is, the decisions, the ones you can't undo, slow them down. It's okay. It's okay. If that term sheet is going to says it's going to explode on Friday, you know what it's not? You know what it's not. Tell the VC you need another couple of days and it will be okay if they want to do the deal. If you're not sure about that m and a term sheet, ask for another week. Ask for another two weeks. It's okay. Be polite, be kind, but explain why it will still be there. And again, if that VP you think you want to hire, you have to make a decision tomorrow or she's going to take another job. Maybe it's best they take another job. Work quickly. But the really big ones, the ones that you that are really painful to undo, slow them down just an extra week and make sure you get the right advice. And when you're sure, do it. But if you're not sure on the big decisions, default to no. Okay. Last of the seven pieces of a big Best advice I've ever gotten the last of the seven pieces of the best advice I've ever gotten on business and then just a few other learnings. The last one's pretty Zen, but this is one that has carried me through the years. And it's so true. There are only a handful of great founders. A handful of great founders and great VPs go all in on them. Look, you will talk if you go along. You will interview hundreds and hundreds of VPs and execs over your career. Only a few will truly make the difference. Only a few will be profoundly change the the needle at your company. The fact that Scott Farquhar, the co CEO of Atlassian, just retired after I think 23 years. But he and Mike made it 23 years together. It's beyond special to see how far Brian Halligan and Dharmesh Shaw went together at HubSpot. You can. Look, some of us can do it all alone. I can't. I'm not successful on my own. I have been so much more successful with a great co founder. I don't think you can do the impossible with a great co founder, but you can do the unlikely with a great co founder. It's such a great multiplier. So whatever you do, be there for them, have their back and just go super long on the best Co founders. Same with the VPs I remember I was with a few years ago, I was with one of the top SaaS CEOs backstage at an event and we were talking about VPs and this is one of the great executives out there. And I asked how many of his VPs were truly great, like truly great. And he had a great insight for me. If you're truly lucky, half your VPs are so great that they do even more than their job. They do even more than job. It's hard enough to find a VP of marketing that can hit the commit, a VP of Sales that can hit the number, a VP of engine engineering that can keep software production going, a VP of product that actually knows the product, et cetera, et cetera. But if you're lucky, once in a while a VP will do more. They'll almost be like a mini co founder. They will care so much, they will go far beyond their job. They'll do far more than just their job, which is hard enough. You're lucky to get one. And if you're half your management team is just epic. You just can't be stopped. It's so rare. And he's right. There's only a handful of great co founders and VPs. When you have one, try not to let them go. They may want to go drag them out of the parking lot, go take them out to dinner at some point sometimes the best do have to go and it's always a bittersweet moment. But make but keep them as long as you can. The best of the best. They're much rarer. You'll look back and realize they're much rarer than you ever thought. Okay. And five quick other pieces of advice t more tactical advice that I got that really made a difference in the long run. Number one, hire someone full time ASAP to manage your big customers even when you have just one or two of them. One of my old bosses said this to me and it was so right again. In my very first startup it was enterprise. So my co founder and I managed our customers. There weren't that many but I, I, I, I sort of got this wrong as I went into a SaaS environment with hundreds and thousands of customers and I, I didn't have enough ownership, full time ownership of those top whales. And so what a lot of us do is we just wait too long. We wait too long to have customer success. We wait too long to support our top customers and it's great if you close them yourself as the founders founder led sales is powerful but you got a lot to do in your 50 hours a week. As soon as you have even one or two mid five figure, six figure customers, hire someone full time to make them happy. It will pay off. It will pay off. Yeah. You may think you need a huge millions and millions of revenue to properly staff your largest customers. No. If you're lucky enough to close a Google or Facebook or Dell or Meta or X or whatever in the early days, you can't lose them. It's such a gift. And you've got to hire someone whose only job is to make those first couple customers successful. 2. This is actually advice I didn't get, but I give it to folks now. It's the, it's maybe the advice I needed to hear, which is that you can go further than you think. You can go further than you think. Most of us as founders are not proven. Most of us have not done it before. Most of us are not second time founders. Most of us did not have a billion dollar exit the last time. In fact, most of us going to the first point of aren't even really experienced managers. Most of us actually have to hire folks over time much better and much more experienced than us. And that is intimidating. But here's the thing. After you've been doing it 18, 24, 36 months, you will know your space, you will know your industry, you will know your workflows, you will know your product in a way no one else ever will. No one else hitting the ground running from the outside will ever get there. It's this special knowledge. And if you combine that special knowledge with drive and spending 20% of your time recruiting, you can scale forever again. How can the co founders of atlassian start at 21 and run the company for 23 years by hiring executives better than them? It's the same story again and again with founders. Yeah, this is tough to do in the early days. You got to try to find a way. But as you scale, you'll find you're able to do this routinely hiring folks under you who are better and more experienced than you are. And that's if you keep doing that and you keep refreshing that and you keep hiring folks that are even more better and more experienced than you. Every three, four, five years, you can be a CEO for 10, 20, 30, 40 years if you want to. Even if you have a lot of imposter syndrome in the early days. Okay, 0.10, 0.10 and then just two more and then we'll wrap this session up with the best advice. It's okay to take a quarter to rebuild. I didn't hear this enough as a founder. I heard it a little bit, but I think this is the advice you hear from the best VCs and board members. It's okay to take a record a quarter to rebuild. You're not public. You're not public. You're not under the same level of scrutiny. So sometimes things are just too messed up. It's often when you make just a really rough hire, especially a VP of sales hire, so many of you will make the wrong hire for your first VP of sales and you will lose quarters or months or even a year, but other positions as well. And sometimes things seem so messed up that there's just no way you can make the quarter. There's just no way you can keep things, things going at the level of velocity that you have to sometimes take a pause for a quarter. Now, this doesn't mean now you can't take a pause for a year, you can't take a pause for a decade. But sometimes it's okay to let the pressure off for one quarter and spend 110% of your energy rebuilding what you need to building another product, building a product extension, rebuilding the management team, breaking through some technical debt that's killing you, downtime that's killing you. Sometimes you really have to pull that, pull that line on the train and stop for a minute so that you can rebuild for the future. I think if you do this once every couple of years, it makes sense. Again, if you do it every other quarter, you'll never get anywhere but give yourself one mulligan as a founder. Give yourself one quarter where not at the end when you can't make it, but at the start of the quarter. Say, listen, the last three, four quarters it's been okay. But we have this big issue in debt and team and others. And I'm gonna take a pause this one time for 90 days and I'm gonna spend half my time fixing this problem. It's okay. It's okay. Okay, second to last piece of advice. Sometimes your best mentors give you advice that hurts. Folks, I'm just gonna say this and I hope some folks listen. Today we're full of the world is full of founder friendly VCs. It is full of folks who tell you what you want to hear. And the last couple years, somehow this has become and even more accentuated, everyone's being told they're doing great, even when they're not. It's happening in startups, it's happening with founders, it's happening with kids in school. Every kid in school is a winner now. Even if you don't attend or ever turn in your homework, good job. You'll surround yourself and you will find VCs and investors and advisors that also often tell you great. Everything's great. Buck up and it is it it. You do need this as a founder. You. You can't. You need a few people who can buck you up, can make you feel better. Don't get me wrong. Hopefully it's your co founder going to earlier point, but the best mentors are going to give you advice that hurts. Folks. They're going to give you advice that hurts. Again, when I talking that earlier story, when one of my first bosses, when things were tough, told me I had to get on a plane and go visit customers, the way he said it was pretty direct. He didn't tiptoe around it. He didn't say, you've done a great job, Jason. But he cut me off. He literally cut me off mid sentence. He said, you're not visiting any of your customers, Jason. You're going to fail if you don't. I could take that today, but at the time it really stung. It stung. I almost still remember that, that pain today. But if the person really cares about you and they know enough about your business and what you're going through, a lot of the best advice is really going to hurt. So be tough, shrug it off, listen to it and realize if the advice that hurts from someone that believes in you, that is better than you, that you trust, if you believe in them, if they're better than you and they trust and they're armed with data, the best advice is going to hurt. In fact, when it hurts, it probably means you should go do something about it. Okay, last point. This is more early stage ish, although it can apply to second acts and second products too. You got to go. There's only so much time. The competition is fierce. Your money only lasts so long. Some of the team is only going to last so long. But sometimes you really aren't ready yet. Sometimes you really aren't ready yet. Both my startups, I launched too early. Okay? The second time with Adobe Sign, with Echo Sign, it was painful. We lost some customers, but it wasn't the end of the world. And software, you can always, if it's just pure software, you can always pretend and do a second launch. You lose momentum, which is a big deal, but you can relaunch. My first startup where there was a hardware component, it was brutal. We actually never recovered from the second largest customer in the industry because we launched too early, because our product didn't work. And what I just learned in both cases is I'm so driven. You're so driven. We want to get it out there. You cannot. Especially in Sask, you cannot launch with 100% perfect product. We don't have time. So 8.5 times out of 10, 85% of the time, just push it out. But sometimes you aren't ready. Be honest. Is your product secure enough? Is it enterprise enough? Are you really ready to launch this? Will you fall on your face? A good plan today is better than a perfect plan tomorrow. But as founders, you have that. You've got to go long and just remember, maybe 10%, 15% of the time, if you're not sure you're not ready to launch, sometimes it does need to go back into the oven for another few weeks, another month, another quarter. And I wish looking back a couple times, I just been a little bit more patient again on these big decisions that you can't undo rather than the small ones. If it's a tiny little feature release you can roll back, great, push it out. But if it's a but, if it's a potential game loser or game changer, sometimes you're just not that you're not ready yet. Okay. Those are my best pieces of advice I've heard, I've learned over the years for general business advice. Hope it saves you a little bit of pain.