Neil Patel

I hope you enjoy reading this blog post.

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Jack Newton is the co-founder and CEO of Clio which is a suite of web-based tools that help law firms in practice management and client collaboration. The company has raised $300 million from top tier investors such as Bessemer Venture Partners, TCV, Point Nine Capital, JMI Equity, and Acton Capital to name a few. 

In this episode you will learn:

  • The two big leaps in scaling your workforce that will challenge you
  • How to create useful company values that help your team
  • Why your real job as a founder is to hire such great people that you can be irrelevant to the organization
  • Embracing the remote workforce


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Jack Newton:

Jack Newton is the founder of Clio, one of the pioneers of cloud-based practice management. Jack has spearheaded efforts to educate the legal community on the security-, ethics- and privacy-related issues surrounding cloud computing, and has become a nationally recognized writer and speaker on these topics.

Jack has recently joined the board of the International Legal Technology Standards Organization (ILTSO), where he will help the organization craft standards for law office technology. He also co-founded and is acting President of the Legal Cloud Computing Association (LCCA), a consortium of leading cloud computing providers with a mandate to help accelerate the adoption of cloud computing in the legal industry.

Connect with Jack Newton:

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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have a very interesting founder from Canada, and I think definitely he has a lot to share. He’s transforming an outdated industry, and I think definitely what he has accomplished so far is very, very impressive. So, I think that without further ado, let’s welcome our guest today, Jack Newton. Welcome to the DealMakers show.

Jack Newton: Thanks for having me.

Alejandro: Originally born in Toronto. How was life there, and also growing up in Edmonton?

Jack Newton: I was born in Toronto. I got a feel for what the big city was all about, and I still have a bunch of my extended family in Toronto and visit there as often as I can. But I really grew up in Edmonton. I went to junior high and high school in Edmonton and did my University degree, my undergrad, and Master’s Degree in Edmonton, as well. A smaller city, about a million people, and very cold. Edmonton gets down to -40 in the winter, pretty frequently, and that’s the same temperature in Celsius and Fahrenheit, by the way. So, cold on either scale. I think that makes for a hearty environment. They are hardcore people that live in Edmonton. My most recent journey westward is to Vancouver, where I live now.

Alejandro: Very nice, and you went to University there, and you specialized in machine learning. Probably, there were not a lot of people talking about machine learning just as much as they talk now about it. Everyone and their mother seem to be doing machine learning nowadays.

Jack Newton: Yeah. That’s right. I was doing machine learning before machine learning was cool. I got the privilege of working with some researchers at the University of Alberta, which is an exceptionally strong school for machine learning. There’s Jonathan Schaeffer, who is a well-known AI machine learning expert. He built some of the best AI for checkers, and later chess, and No-Limit Texas Hold’em poker, the best poker-playing AI on the planet back in the early 2000s. And this was a very interesting fork in the road for me back in the early 2000s was, when I had done my Master’s deciding whether to go into industry or into academia. I was being recruited by the University of Toronto. I had to go to my Ph.D. with a great scholarship and an amazing professor to work with who was Geoffrey Hinton, who was already really well-known in the machine learning community at that point in his career, and obviously with the impact that his neural networks work has had over the last decade. He’s an order of magnitude more well-known now, but very interesting to think about what an alternate path for me might have looked like had I gone the academia route rather than industry.

Alejandro: Got it. It’s amazing how you have applied your knowledge and how you have been jumping from one industry to another. Here you go from academia. You go into startups, into medical diagnostics, and then to legal. It’s really interesting how you jump from one industry to another. So, let’s go with the first jump. Going into medical diagnostics and really getting a feel for the world of startups. How was that?

Jack Newton: Yeah. It was actually really interesting. I was between my Bachelor’s and Master’s Degrees when I got my first job out of school, which was at a company called Chenomx. What Chenomx was doing was building medical diagnostic software in this industry that was really old-school, doing these assays that took days or weeks of time to complete, and often took thousands of dollars of investment to get this assay of potentially 100 or 200 metabolites assessed. What Chenomx was working on was this fascinating technology to use high-field nuclear magnetic resonance technology, which is basically a flavor of MRI. If your listeners are familiar with Magnetic Resonance Imagery, this is the same concept applied at a much higher field strength, much more powerful field strength to small biofluids. These biofluids could be cerebrospinal fluid; they could be blood; they could be urine. What you look for in these biofluids are metabolites. With a single one-minute scan from this Nuclear Magnetic Resonance or NMR machine, you could get a complete view of every metabolite in that biofluid. I became Software Developer #1 at Chenomx when I was referred there by one of the professors I was working with at the University of Alberta. I basically went there after my Bachelor’s Degree and started working on this problem, and rapidly realized that I had no idea how to solve the problem. I was fundamentally ill-equipped to solve the very complex machine learning/AI problem that they had to solve at Chenomx. That was a catalyst for me to go back to school and do my Master’s Degree in machine learning because I found this whole area so fascinating. I went back to school and did my Master’s Degree in two years, and actually went back to Chenomx two years later with a smile on my face saying, “I know how to solve this problem now,” and got to work. What was really interesting was, in those two years, the company had raised about a million dollars. It has grown from four people when I joined to over 25 people when I returned, and I came in as the Director of Product Development and got to work on the go-to-market strategy and the technical aspects of solving this diagnostics problem. Through the exposure of fundraising and building this product, I caught the startup bug. I became really passionate about the idea of building startups.

Alejandro: It’s interesting because here you worked for quite a while. We’re talking about five years or so that you were working for the business. You really got to see the inside and the other side of being in the startup itself. Why did you decide, “I’m going to do it myself”? At what point did you decide, “I’m going to take the leap of faith. This is my time to go at it and make it happen.”

Jack Newton: It was an interesting journey. For me, one of the realizations at Chenomx when I had been there for a few years after finishing my Master’s Degree was, I’m having a ton of fun. I love doing this, but I started to get the itch to do it myself, to have the increased stakes of being the founder, going out and fundraising, and building something from scratch. I was always highly entrepreneurial. When I was growing up, I had a variety of both successful and unsuccessful ventures that I would experiment with everything from planning a snow-shoveling service in Edmonton, which, as I mentioned, the weather was often horrible. The snow-shoveling business where I had a network of snow-shoveling employees, mainly made up of my brothers and did a booming business. I had launched a flavor of an early focused on food delivery to remote communities in Canada. My co-founder, Ryan and I have known each other since we were eight years old. We actually met in elementary school in Edmonton. We had, for years, been wanting to do something entrepreneurial. We dreamed of building our own company from scratch, and we became increasingly passionate about this idea that we could build a lifestyle business together. If this business threw off $100,000 a year, we would call that a big success. So we were looking for an opportunity to build this kind of a lifestyle business. Back in 2007 or so, we saw the Cloud as one of these once-in-a-lifetime technological transformation waves that was going to fundamentally alter and transform almost every industry on the planet. We, at that point, became two hammers looking for a nail. Ryan was working at Gowlings, which is one of the largest law firms in Canada with over 1,000 lawyers. I was at Chenomx, and we started looking for an industry that could benefit from the impact of Cloud technology. Thanks, in a large part, to Ryan’s exposure to legal technology that Gowlings was using, and Ryan witnessing firsthand how awful that technology was, frankly, we rapidly honed in on legal as this gigantic opportunity. We started slow. We started investing in market research. We were surprised to find that there was no competitor for our idea, a cloud-based practice management system. We’re going to be the first to market with any kind of solution within this space, and we started bootstrapping. In the early days, we did not make any kind of grand jump out of the airplane and pull parachute on our day jobs. For the first six months or so, we were moonlighting and working on this project on the evenings and weekends and trying to get a prototype built that we could then test with the market. By the time we raised our first $100,000 of friends and family funding back in 2008, we had some good early indications from the prototype we’d built that we had product/market fit, or at least, very early product/market fit. By the time we pulled chute on our day jobs and went all-in on Clio, we actually had a lot of data that this was going to work out. One takeaway lesson for me that I often advise other prospective founders is, you can get a lot of data and a lot of certainty around whether your concept will work without necessarily going to the risk of being all-in from day one. I think where the real art and science come in is the judgment call on when do you pull chute and go all-in because it’s never going to be a totally safe thing to do. But you need to be disciplined about when to make that call because if you don’t go all-in at some point, your idea will always remain a side project and will be doomed to sit on the shelf and never get executed against the way it maybe deserves to be.

Alejandro: Of course. What I want to ask you here is, do you think you guys went all-in? If you could go back again, would you have given your notice earlier?

Jack Newton: It’s a great question, and I do think I would have gone all-in earlier with the benefit of hindsight. I think one of the things I was up against at the early founding days of Clio was we had a mortgage of a house, I was recently married, my wife and I had our first kid on the way. So the stakes felt really high for me at a personal level. I think the toughest thing when you’re making that jump, even when the risk is maybe reduced over what it was previously, you’re still up against the odds. You’re still up against the odds that nine out of ten startups fail, and you’re really taking a gamble that you’re going to be the one out of ten that makes it. But I think that if I could do it all over again, I would go all-in from day one. But I do think that that’s only with the benefit of hindsight and only the benefit of knowing that Clio worked out, and we were extremely lucky that our first idea turned out to have the traction it did. I take this kind of approach of placing measured beats has the benefit of allowing you to make potentially multiple beats and to try multiple ideas before you potentially find the one that is going to stick and have the impact.

Alejandro: Of course. For the people that are listening, what ended up being the business model of Clio? How do you guys make money? 

Jack Newton: It’s a very simple Software as a Service subscription model. Our early pricing was $49 a month per user, and you just simply pay as you go, and you pay as you scale your usage of Clio. For the first six months or so of our development, we were completely free as a beta product, so we were getting early feedback on the product, early customer discovery understanding who our customers are, and what features they need. We actually iterated on the product rapidly because we discovered a few of our fundamental assumptions about what the product needed to do, and didn’t need to do, or incorrect. And between March of 2008 and October of 2008, we went from a beta version that was free of charge for beta customers to our very first paying customers paying us $50 a month and up in October of 2008.

Alejandro: Very nice. I know that you guys also tried fundraising in a downturn. So, what did you learn from that? I’m sure that you got some good lessons that maybe you can apply now to what we’re dealing with, with the coronavirus.

Jack Newton: Yeah. I look back at our timing, which I think our timing was perfect through one lens and awful through another. When you look at the timing for the market, I feel like we were launching the first Cloud application in legal at precisely the right time, where there were just enough early adopters for us to get traction with and to start to scale. I think from that perspective, our timing was bang-on, and if we were even just a year earlier, I think we probably would have failed. And if we were a year later, there would have been competition that had already established a foothold in the market. I think we nailed the timing by sheer luck in that sense. From a fundraising perspective, we started trying to raise our Series A. A modest Series A by today’s standards of just a million dollars in 2008/2009, which was the height of the financial crisis related to the housing market collapse in the U.S. Much like today, the mentality, it’s easy to forget how severe the mentality was in ’08, ’09. But people really feared the economic system, as it existed, was going to collapse, and that all bets were off, essentially. I think you see some of the same things in the COVID-19 world that are today where people are legitimately worried that the economy is not going to look anything like it did pre-COVID-19. In ’08, ’09, just like today, many investors put away their checkbooks and said, “We’re going to wait this one out, and we’ll let you know when we start writing checks. We actually had a really frustrating and almost demoralizing process of trying to raise money in ’08, ’09 beyond that $100,000 that we raised from friends and family, which was relatively easy to raise, thankfully, and had the good fortune of a network of friends and family that were willing to write a check for us, even with my disclaimer that they should treat that investment as if they were lighting the money on fire. I really made it clear to my friends and family, especially my family, that I did not want to be coming to a Thanksgiving Dinner down the road where my mom and dad are eating macaroni and cheese for dinner because they lost their nest egg on Clio. I wanted to make sure people were only investing what they viewed as discretionary funds. We put that $100,000 together. But the next million was unbelievably hard to raise, and it was pounding the pavement. We went to every western Canada angel forum that existed. We pitched to VCs from the Valley and heard really frustrating feedback, which was, “This is a great pitch, a great concept. We think you’re going to be successful. We’re just not writing checks right now. It was a really, really demoralizing process to try to raise money in that time period. My takeaway to your listeners that may be experiencing some of the same frustration in the COVID-19 world is just to hold on and to keep that optimism out because the thing that can be very easy to do is to conflate the quality of your idea and conflate the quality of your execution with the market reaction that you are getting that are solely due to a macroenvironment out there. And realize that the macroenvironment will see a turnaround eventually, just as it did in ’08, ’09. We went from a recession and a downturn that everyone was putting away their checkbooks to a bull market that lasted for more than a decade starting in 2010. This too shall pass is my advice and to try to maintain your conviction that your idea is a great one, and that it will get funded, and to do whatever you need to do with your burn rate to try to get to the other side of this.

Alejandro: That’s amazing. I know that for you, there’s quite a funny story that has to do with spam filters and your first investor. What happened there?

Jack Newton: This is one of my favorite stories of my Clio journey. It was related to this fundraising cycle. Like I said, we were demoralized, we were feeling like we had explored every avenue. We had gone fairly far down the line with a few investors that had ended up pulling a bit of a bait-and-switch on us and tried to jam a really bad deal down our throats. So, we were feeling pretty dejected at this point. One day, my co-founder, Ryan, was on a phone call. I think it was a customer support call that was dragging on and on forever, and what I can only describe as an act of God, Ryan decided, I think for the first time ever, and I don’t think he’s ever done it since, to check his spam folder and see what was in there. Just to give you some context, we at an early version of what is a G Suite, so we had the corporate version of a Gmail app, and Ryan decided to check out “What’s sitting in my spam folder” while he’s on this endless support call. He sees an email from Christoph Janz, which was an inbound email basically saying, “I heard about Clio on this blog called It was a blog that happened to be run by a good friend of mine, Reg Tremie, in Edmonton. He had written a blogpost about Clio, and this cool startup, his friend, Jack, was building. Christoph happened to stumble across it. Christoph was based in Germany, sent this email inbound to us, a cold email saying, “I’ve read about Clio. It sounds like a super interesting idea. Love what you guys are doing. I’m a founder that recently sold his company, and I’ve now turned into an angel investor. I just completed my first angel investment in a company called Zendesk, and this was when Zendesk was four guys in Copenhagen, and Christoph was the first angel money into Zendesk. He said, “I’d love to make Clio my second investment.” The irony here, by the way, the story gets better. There was a follow-up email from Christoph two weeks later because we had inadvertently slow-played him by ignoring his initial email. He sent a follow-up email saying, “I just wanted to reiterate. I’m really interested in what Clio is doing and would love to invest if it’s possible. Sure enough, we followed up with Christoph. Ryan forwarded me the email and said, “This looks legit.” I followed up with Christoph, and he cut to a few months later and a bit of due diligence and a 24-hour trip to Germany by Ryan and me to meet Christoph face-to-face. We had a deal done, and Christoph ended up leading our million-dollar Series A. Truly, deus ex machina kind of event for us, where we discovered this amazing investor, and I’ve only got the best things to say about Christoph. He’s now running a very successful VC firm called Point Nine Capital out of Germany, and he’s the most incredible investor. We’re so lucky to find him, or maybe better put, to have him find us. It was literally a fluke. His email to Gmail had all the hallmarks of a Nigerian scam email. He was offering us money. He was emailing us from a web.dee address, which probably looked like a really sketchy email address to Google. He ended up leading our round. So, it was a huge amount of luck and good timing to run into Christoph, and like I said, he’s been an incredible supporter. Clio wouldn’t be the company it is today without Christoph’s support.

Alejandro: And the rest is history. How much capital have you guys raised to date?

Jack Newton: The rest is history, absolutely. I jokingly say, but I’m actually quite serious, as well, that first million dollars was the hardest, and once we started to invest that million dollars and really started to demonstrate the scalability of our business model and the fact that we could bring more and more customers to the platform, we then raised a 6 million dollar Series B, led by Acton Capital. Then, in 2016, we raised a 20-million-dollar Series C, led by Bessemer Venture Partners. Just this year, we announced our 250-million-dollar Series D, led by TCV and JMI Equity. We’ve now raised the better part of 300 million dollars in building Clio. As I said, that first million dollars was definitely the hardest, and once we started to show some real traction and started showing that we were successfully transforming this industry that by-and-large has not adopted technology over its entire history, that we’re starting to drive this fundamental change, we started to see some real inbound interest from investors.

Alejandro: Absolutely. Here, what I want to ask you is, now that everyone is adapting to working remotely and to the new back-to-normal. That back-to-normal is a normal that we don’t know. It’s definitely not going to be back to normal; it’s to the new normal. Right? In that new normal, people are going to be adapting, and I know that you guys were already thinking about this quite ahead, and you started already being remote. So, would you mind expanding on that a little bit?

Read More: Fahri Diner On Selling His First Startup For Over $3.5 Billion And Now Raising $150 Million To Make Your Home Smarter

Jack Newton: Yeah, absolutely. As I mentioned, we bootstrapped Clio in the early days, and Ryan, at that point, had moved to Vancouver to pursue his Bachelor’s Degree and, eventually, his Master’s Degree in business administration. When we started working on the idea that turned into Clio, I was working in Edmonton, and Ryan was working in Vancouver, we figured out ways of collaborating remotely. We were using web-based chat tools and some of the early video chat tools to collaborate and to work together and embrace these precursors to Slack, like Campfire and HipChat. We also started hiring our first handful of employees. Once we raised that million-dollar Series A and started hiring employees, we were hiring those employees in a distributed way. I was hiring a pocket of employees in Alberta. Ryan was hiring pockets of employees in B.C., and those employees, likewise, found ways to work with each other in a distributed way. As I mention to our team frequently, we’ve got remote work built into our DNA at Clio. I think we’ve always focused on a high-quality experience for our employees in this remote-work situation and have always invested in basic things like good AV and good remote worker accommodations in the sense of high-quality video chat here in our offices and so on, and have always had remote work as part of our culture and part of our DNA at Clio. I feel like that’s served us to tremendous effect amidst this COVID-19 crisis where back on March 13th, I told the team, “We’re shutting down all five of our worldwide offices, and we’re sending 500+ employees to work from home. We enforced a mandatory closure of all of our offices. What truly amazed me was I think partially because of this remote work DNA and strength that we’d built up over the better part of 12 years and the fact that we drink our own champaign in that we completely adopt cloud-based tools at Clio. We didn’t have any on-premise systems or any hardware that employees need to access beyond their laptops. We were able to send everyone home. It was remarkable. I sent everyone home on a Friday, and by the time everyone was logging in and starting to do their job on Monday morning, I realized we’re not going to miss a beat here. This is phenomenal, and we were literally able to translate into this work-from-home environment and having 500 distributed employees working from home in a really successful and seamless way. 

Alejandro: That’s super cool. Talking about people, I know that going from 50 to 100 employees was a bit tough for you. Why was that the case?

Jack Newton: There are a bunch of things in the growth story for Clio, a bunch of chapters that I think about as being challenging, but one of the most challenging periods of growth for me, personally, and for the company was in scaling from 50 to 100 people, and then from 100 to 200 people. Those are two very distinct growth phases, but I think what you’re seeing in the first growth phase from 50 to 100 people is this growth phase where not everyone knows automatically what the company’s values are and what the company’s priorities are. When you’re less than 50 people, if you think about the days when you’re a 10 or 25-person team in a startup, everyone just automatically knows what’s going on, what’s important, and you’ve got this almost intrinsic culture that has just been created organically through the people you’ve hired, and maybe the people you’ve fired, and the people you’ve promoted, your culture is forming, and you’ve got to give it a chance to evolve to a real final state. On the value’s front, what I found was that everyone felt, at 50 people, for example, that we had a special culture at Clio, and we had a special set of values, but nobody could actually articulate exactly what those were. Nobody could put their finger – we didn’t have a list written out of what our core values were. One of the things we did as an exercise when we were around 75 people or 20, was, we went through an exercise of defining our values, and we made it a grassroots thing where we asked the team at that time, “What do you see as the things that make Clio special? We all think that we’ve got something special here. We know that we’ve got something special at Clio, but how do you put your finger on exactly what it is that makes Clio special. So, people started to write down and brainstorm what they felt the real pillars of Clio’s values and culture were, and we ended up with our seven core values as a result. The most critical role values can play is to be looked at almost as the rules of a sport that you’re playing at your company. They’re the rules of the sport in the sense that you’re saying this is what success looks like – people living these values is how we will make promotion decisions, for example. It’s how we’ll make hiring decisions. It’s how we’ll also make firing decisions. I think if you’ve got your values written out and they’re explicit, they’re carefully thought out, and by the say, they’re opinionated, I think it’s important to have values that suggest a tradeoff. You can’t just have values that are empty, for example, and suggest something that might be tautologically true. We have integrity; we act with integrity. Great. How does that help you make a hiring decision? How does that help you make a decision any time? It’s not something that suggests a tradeoff. For me, that’s where the most powerful values come from is a place where you are making a tradeoff decision, and you’re saying, “I will prioritize x over y,” and that can help employees make great decisions. Then, when you’re hiring, values that are written down can be enormously powerful in that you can be transparent with candidates and say, again, using the sports analogy, “Here’s our rulebook. If this doesn’t sound like a sport you want to play, if this doesn’t sound like a ruleset, you want to be measured against, no problem – no pressure. We will happily part ways here, and you can go find a company that’s a better fit for what your internal value system might be. So, when you think carefully about your values, and you start to get to a point where you can write them down, and articulate them to your team and articulate them to potential hires, it opens up the opportunity to scale rapidly. I think that’s where a lot of startups fall down is in the scaling journey from 50 people where things are working great to 100 people. Then, crucially, this 100 to 200-person journey where you’re going through the Dunbar number, for example, and you’re passing that 150-person threshold, where you lose the ability to internalize everyone in the company and understand what makes them tick and feel socially connected to everyone. If you don’t have somebody’s foundational systems like a value system established, that’s where you see the wheels fall off, and that’s where you see companies dilute their culture, starting to lose their way, and often imploding or, best case scenario, staling out with respect to their growth. The other thing that I found to be instrumental in this journey from 50 to 100 to 200 people was establishing a goal-trapping system to articulate what is most important to the company, and how does that map down to what is most important for each department, and what is most important for each employee? We adopted this system that’s widely adopted at startups today called OKRs, objectives and key results. This is a system originally pioneered by John Doerr at Intel. It has been adopted by some big tech companies like Google, and it’s a straight-forward goal articulation system where you list you high-level objectives and the quantifiable key results that are in service of that main objective, but it’s so powerful because, again, when you’re 50 people, I think everyone often just intrinsically understands what the priorities are for the company and what they should be working on to support that priority. When you get to 100, 150, 200 people, you’re getting to a scale where if you’re not using a rigorous goal-tracking system, you can often see people working on what they think is high-impact, but it’s actually out of alignment with maybe what the company really cares about and what the company priorities are. You need a system that will help you scale and will help each individual contributor of your team understand how their efforts are laddering up to the company level impact that everybody wants to see, but they need a system that they feel they can tie into that should translate that impact into outcomes that are moving the needle for the company.

Alejandro: Of course, John Doerr has a very nice book on this, the OKRs.

Jack Newton: He does.

Alejandro: I think it’s a good book, so the listeners should check it out. I want to ask you something, and it’s a question that I typically ask the guests that come on the show, and that is, knowing what you know now – you’ve been at it for about 12 years with Clio. If you had the opportunity to go back in time and give yourself one piece of business advice before launching a company, what would that be and why, knowing what you know now, Jack?

Jack Newton: I think I would focus on the advice around hiring a senior leadership team, hiring an executive team more aggressively than feels natural. I think what every founder or CEO needs to be aware of is that as soon as they start seeing product/market fit, as soon as you’ve got that traction starting to happen, your full-time job should become recruiting somebody who is better than you at every aspect of your job and progressively trying to make yourself relevant to the business. That’s actually the best-case scenario, which is a bizarre thing to think about yourself wheeling toward, but realize that you’re never actually going to become irrelevant to the business. But from a domain expertise function, I should not be trying to scale myself in terms of becoming the best marketer on the planet or the best salesperson on the planet. My energy needs to be going into recruiting the best marketer on the planet, recruiting the best salesperson on the planet, recruiting the best product leader on the planet and giving them the autonomy to go and [42:20] job, and focusing my energy on the leadership and vision for the company. I think for founders, especially in the early days, you’re used to doing everything, and it’s literally almost inverting your mindset to one where you’re saying, “I’m doing every job, and I’m wearing every hat, to saying, I am rapidly taking these hats off and giving them to other people as quickly as I can. That juncture where you need to abruptly shift gears is all around product/market fit. I think if I had the clarity of vision around what I needed to do as soon as we started to see that real product/market fit take hold, in 2010 or so, I would have been much more aggressive at recruiting that executive team that could help us scale over the next decade.

Alejandro: Got it, and very profound. So, for the folks that are listening, Jack, what is the best way for them to reach out and say hi?

Jack Newton: I’m on Twitter @jack_newton and feel free to shoot me an email at [email protected].

Alejandro: Amazing. Well, Jack, thank you so much for being on the DealMakers show today.

Jack Newton: Thanks a lot for having me.


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