Episode Summary
“I think for us [growth equity investors], you need to have exactly half of it figured out. No one has it all figured out, but, for example, the most common scenarios, one where it’s very clear that you have high product quality and high customer sat and a great market opportunity, limited competitive dynamic, great team, but maybe the founder and his right or left-hand man or woman are doing all the sales. And we would say amazing business. I think we need to work on a more repeatable sales team and hire a sales ops person. And, and you really emphasize that the founder shouldn’t be doing the sales anymore, but that’s still is a great opportunity because you’ve proven the market. You’ve proven the product customers love you. And there’s just a couple of things to fine-tune. And in addition to fine-tuning it, yes, you have the gasoline on the fire analogy is a good one in the growth stage.”
-Jack Freeman, Principal, PeakSpan Capital
Startup growth and navigating the investment environment is a complex game. Greg has been there and done it multiple times, and he’s realized every, single time it’s new. Greg’s guest, Jack Freeman and he will share Jack‘s path from startup to the investor seat. What he’s learned, what he’s still learning and some new areas that he’s getting into. Jack will also share what founders and tech leaders should know about the supply chain landscape.
In this episode, you’ll get insights from yet another supply chain tech pro who’s been there and done it. Jack has been doing investments, mergers and acquisitions. He can help decode the language between founders, executives and investors to help everyone overcome the challenges, successes and enlightenment that he’s seen.
Enjoy this valuable learning opportunity with Jack Freeman, Principal at growth equity fund PeakSpan Capital. Jack leads PeakSpan’s supply chain practice. He has spent his entire career in tech, mergers & acquisitions, and growth capital. Jack currently advises and is invested 12 companies. He’s an avid cyclist, a marathoner and a semi-retired soccer player. Full Disclosure: Jack and I worked together after he recruited me to be a Sector Expert, working with supply chain techs for PeakSpan.
Episode Transcript
Intro/Outro (00:03):
Supply chain is one of the hottest topics in the world right now. And supply chain investing is at a level never before seen. Join me and Jack Freeman from PeakSpan Capital as we talk about the ideal supply chain scenarios, companies, even investors, and some of the most important things you can expect from supply chain evolution over the next years. It’s time to wake up to TECHquila Sunrise. I am Greg White, your supply chain tech advisor, with more insights into what you need to know to succeed in supply chain tech startup growth, investment, and transformation. So, let’s tip a glass to another enlightening TECHquila Sunrise.
Greg White (00:59):
Startup, growth, and navigating the investment environment is a complex game. I’ve been there. I’ve done it multiple times. And every single time it’s new. My guest and I will share his path from startup to the investor seat, what he’s learned, what he’s still learning, and some new areas that he’s getting into, and what founders and tech leaders should know about the supply chain landscape. So, by the end of this episode, you’ll get insights from someone else who’s been there and done it. And someone who’s doing mergers and acquisitions today. And who can help decode the language between founders and executives and investors and help everyone benefit from the challenges, the successes, and the enlightenment that he’s seen.
Greg White (01:49):
So, let me introduce our guest, Jack Freeman, Principal at growth equity fund, PeakSpan Capital. He’s in charge of the supply chain practice. He spent his whole career in tech, in mergers and acquisitions, and in growth capital. He’s currently advising and working with and investing in 12 companies, 12 of PeakSpan’s portfolio companies. He’s an avid cyclist, a marathoner – foolishly – and a semi-retired soccer player. He’s leading their practice. I said in the supply chain space in full disclosure, he and I worked together after he recruited me to be a sector expert for PeakSpan. So, Jack, thanks for joining us. Welcome to your very first TECHquila Sunrise. Are you ready for the real start of this interview?
Jack Freeman (02:41):
I am ready.
Greg White (02:43):
All right. Cheers.
Jack Freeman (02:46):
Cheers.
Greg White (02:55):
Okay. I think we’re ready now.
Jack Freeman (02:55):
What a start. Thanks for having me on.
Greg White (02:59):
Yeah. Well, great having you. This was tough to put together. Putting our schedules together has been difficult, so I really appreciate you being flexible. Look, I feel like I’ve known you for longer than I have, but the thing that struck me is how many companies that you’re partnered with currently. That’s an incredibly exciting challenge. So, tell our listeners a little bit about what you do and explain also kind of PeakSpan’s position in the marketplace and also a little bit about what growth equity means just for those that might not know.
Jack Freeman (03:35):
Absolutely. And thanks again. I think it makes sense if I start with that question. I’m going to start with who PeakSpan is, what growth equity is, you know, all that, because it can get confusing in this landscape where there’s just a ton of investors.
Greg White (03:53):
No doubt.
Jack Freeman (03:53):
I’ll then back up and give you my personal background. And I want to weave in the question you asked me ahead of time, which was, why supply chain? Why am I passionate about it? And that question in my personal background, you’ll see are very interwoven, and we’ll get fun with it. So, PeakSpan, we’re a growth equity firm. And for anyone who’s talked to or heard of venture capital, growth equity, private equity, it sounds just like a lot of noise and there’s a million different ways to invest. The way I would paint the landscape kind of layering on risk appetite and then some strategy. But on one end of the spectrum, you have venture capitalists. The earlier you go, in my mind, the more, “I don’t understand how they do it.”
Greg White (04:45:
More risks, right?
Jack Freeman (04:46):
Investing in Amazon or Kupa before it had a dollar revenue. You’re a genius, because your seed stage investors, it’s voodoo, a lot of risks, a lot of reward. Those are the returns you read about, where Bill Gurley, you know, makes a $10 billion on Facebook. So, it’s the early burst, stuff like that. Then, on the other end of the spectrum, you have private equity. Those are more established businesses. I would say private equity, at the earliest, is getting involved, depending on the firm, like, 20 million in revenue. And for the most part profitable businesses. The most traditional private equity firms in the upmarket ones are going to focus on 20 to, like, a billion in revenue and serious profitability. And the things that private equity folks will do involve using debt to finance a transaction, using the ability to service that debt, et cetera, et cetera. Often, you know, bringing in new management, making big whole holistic changes.
Jack Freeman (05:55):
We’re in the middle, and that’s growth equity. Growth equity are businesses that have real revenue, need capital to grow, may one day be a candidate for private equity, may go public, may get back to profitability. You don’t really know. There’s a lot of decision-making in the growth stage. I would define growth stage by terms of revenue as about 3 million in revenue to that 20 million mark. When you get through that 20 million mark, you could still be raising from growth equity firms, of course. But that’s the segment that we broadly play in. And then, within growth equity, I always say we are emerging growth equity. What does that mean? It is the stage right past venture capital.
Greg White (06:41):
So, if you put an alphabet letter next to it, Jack, what letters would you be?
Jack Freeman (06:46):
The letter is tough nowadays.
Greg White (06:48):
No kidding.
Jack Freeman (06:49):
Yeah. It’s getting really confusing. I’d say we are looking to partner with bootstrapped or the capitalized businesses, so less than 10 or 15 million raised in prior funding is where PeakSpan would be a perfect fit. That could be in a Series A. It could be a Series C. If there was just a couple of small rounds and they decide to call them A and B, but we are 15 million raised or less. Once you get to that 15 million raised mark, things are going right. You’re probably hiring revenue and raising larger and larger rounds and a better fit for a later stage growth firm.
Greg White (07:27):
Cool. Very cool. And you mentioned 3 to 20, so that’s down quite a bit in what seems, like, relatively few years. But as I look back, it’s probably in the last ten years that it used to be for growth equity, it was 5 to 10 was the minimum, and usually it was really ten but if somebody wanted to get an early look at you they would consider you at five. But it sounds like investors – and this has been happening for some years – have come quite a bit down the revenue scale. Share with us a little bit why that is.
Jack Freeman (08:05):
It’s a great topic and we can do a whole podcast on just –
Greg White (08:09):
We could. Yeah. Maybe ten seconds long.
Jack Freeman (08:11):
Ten seconds is fine. So, two reasons I’d call out, which I think we may come back to later in the call just because it’s a friend of mine, for me, and in talking about investing. One is, there is too much capital out there and too little high-quality companies to invest in. The best example of this – and maybe a second reason – is software is eating the world and investors love software. They love the recurring revenue business model, the predictability, the innovation, the growth of the sector. For those reasons, because there’s so much capital out there, so many firms, and so few opportunities to invest in software, there’s this big supply demand and balance.
Jack Freeman (08:55):
The latest headline you can Google is Tiger Global, big [inaudible] invest in public companies. They’re the highest volume issuer of term sheets in 2021. They are, you know, kind of investing like gangbusters for at the —
Greg White (09:13):
For a week. I think I heard somebody say something like that, right?
Jack Freeman (09:17):
I think. I don’t know this firsthand. I think it’s similar to SoftBank’s [inaudible], like, two years ago, which was more series D, E, and F. Tiger Global, I suppose their thesis is, we want as much exposure to software as possible. We’re going to go at the earlier stage and do a higher volume, fund a lot of exciting companies. And I don’t know what that risk return model looks like for them. But it just shows that there’s a lot of capital, hedge funds are getting down into growth equity now, and there’s a lot of interest.
Jack Freeman (09:54):
The other reason I would say just from our perspective in software as a service is, when you’re thematic and when, let’s say, looking at a supply chain business, because there’s more data out there and more sophistication around SAS, I always tell entrepreneurs, “We have a $3 million error minimum.” If that’s three customers, you’re still too early. If that’s a hundred customers at, you know, 10K a customer, that’s a lot of data. You can analyze a lot of retention data, sales efficiency, product market fit, customer references. That could be a pretty mature business. And I think that’s part of the reason why PeakSpan feels comfortable. We previously drew the line at five. Now, we’re drawing at three, because there’s a lot of interesting businesses that are proven out their go-to market and business models at that scale.
Greg White (10:46):
And I think that’s an important distinction, Jack, is, you know, venture capital is highly speculative. You know I work with Kubera VC also, and that’s pre-seed, seed, and A round. And then, we’re done investing at that point. But we’re looking for companies that are still looking for, as you said, that product market fit. They don’t have it figured out yet, but they’re well on their way. By the time they come to growth capital, would you say it’s a fair bet to say these companies have it figured out? And, now, what they need to do is put fuel on the fire to really, really accelerate. Is that –
Jack Freeman (11:26):
That’s exactly right. I think for us, you need to have exactly half of it figured out. No one has it all figured out. But, for example, the most common scenarios, one where it’s very clear that you have high product quality and high customer sat, and a great market opportunity, limited competitive dynamic, great team, but maybe the founder and his right or left hand man or woman are doing all the sales. And, you know, we would say, “Amazing business. I think we need to work on a more repeatable sales team and hire a sales ops person.” And really emphasize that the founder shouldn’t be doing the sales anymore. But that still is a great opportunity because you’ve proven the market, you’ve proven the product, customers love you, and there’s just a couple of things to fine tune. And in addition to fine tuning it, yes, you have the gasoline on the fire analogy is a good one in the growth stage.
Greg White (12:28):
Yeah. Or opportunities to capture additional market share or additional markets with expansion of that finely tuned product, right?
Jack Freeman (12:41):
It’s another great way to look at it. There’s usually some sort of thesis on why are you raising growth capital. It could be as simple as, we have this go-to market model, it’s baked, and we want to spend more on sales and marketing. I would say a self-serve product. We invested in a company called Ecwid, an e-commerce platform, similar to Shopify, but with an API centric approach. They don’t have an outbound sales team. They’re fully inbound, self-onward, self-serve, and their go-to market is partly through channel partners, partly through direct. That’s an example of a business model where they were spending X on marketing. When we came in, they don’t need a ton of capital because they’re very capital efficient. But allowing them to double or triple the marketing budget in the few quarters following our investment just was more of that.
Jack Freeman (13:36):
You probably heard the dials and knobs analogy, where you have your business dialed in, you can crank up marketing spend, and increase revenue. That happened some of the time. But in enterprise software and supply chain, you know, that’s not the case. It’s a lot more complex building a pipeline of enterprise customers and making that predictable. That’s not necessarily a dials and knobs business versus a strategic sale, knowing your ICP, and your customer base, and intelligently targeting that ICP in a way that’s predictable and scalable. So, sometimes it’s straightforward as marketing dollars and other times it’s less straightforward.
Greg White (14:18):
So, I think we’ve already established a couple of things. And one is that you’re way smarter than I am.
Jack Freeman (14:30):
No. It’s the tequila talking.
Greg White (14:33):
Mine or yours? Who even remembers? So, I’m really interested in learning about your interest in supply chain, but before we jump into supply chain, let’s talk about a couple of other, I think, formative moments for you. Well, one is, you obviously are invested in currently a dozen companies that – or nearly a dozen that have given you a good flavor for broad spectrum of types of texts. So, what is the most fascinating, or engaging, or interesting, or motivating part of investing for you?
Jack Freeman (15:15):
Great question. I think my job that’s [inaudible] before this, the three areas I would call out, one is the people. So, unlike other categories, consumer nanotechnology and hardware where – to use your example – you actually do have to find smart investors who are savant and geniuses and know nanotechnology to, like, the next chip maker or the next Elon.
Jack Freeman (15:50):
Unlike those investments, at our stage and in SAS, yes, the technology is important. But you’re investing behind people. People are the biggest risk and also the biggest reward in a growth stage software investment. We’re analyzing markets, supply and demand drivers, competitive analysis, e-economics. Actually, it’s not rocket science. But what is very difficult is analyzing people, and understanding people, and who’s going to make a good leader, and who can build a scalable culture. So, to your point, we’ve worked with 15 partners at PeakSpan, and the number one learning is, how important it is to partner with the right people, good entrepreneurs, collaborative founders. And those things can’t really be taught. They’re more learned through experience. That’s one. I can name two others, if you want.
Greg White (16:57):
It’s your call, man. I mean, mostly I love the people aspect of it. Because you get to meet so many collections of people that are making great things happen. But, yeah, tell us what else.
Jack Freeman (17:15):
Cool. These two are more supply chain-centric, so I like these. The second also has to do with – actually, all three have to do with people. It’s great. Second one in terms of people is, in the segments that I look at it in supply chain, procurement is another good one, where you can have a great technology and a great idea and not go anywhere with it because you have to convince people on the other end of the phone to adopt your technology, one. Sometimes champion it and, like, love it so much that they’re going to turn around and present it to 60 people at their enterprise and say, “Hey, I’m Jack. Spend $300,000 on this software and change all of your internal behavior to do a display. Greg and Greg’s company said that’s the right way to do supply chain. Here’s some slideware and let’s just change the face of what we do using technology, because I think it’s a great idea.”
Jack Freeman (18:21):
Convincing a human to stick their neck on the line for your software is the hardest thing to do. The folks that can do that type of strategic selling and just helping build champions at enterprises is where you make very valuable companies. And I don’t want to belittle product and engineering. You need amazing product and engineers to build it. The product needs to be intuitive. People need to love the product. For example, I’ll compare it to Asana. I’m a power user of Asana. I’ve used it for eight years. There’s no, like, enterprise sale – they do enterprise sales, I guess – but mostly it’s product like growth. The product is what drives adoption. In a lot of the segments, we look at it in supply chain and procurement, the company’s ability to drive adoption and change management is just as important as the technology itself, that’s two.
Jack Freeman (19:21):
Three is, again, another supply chain one, but just tracing back everything to supply-demand dependencies and why something is important. Looking at e-commerce logistics technologies, why is that important? Because e-commerce has boomed over the last 12 months and has been really booming for the last few years, and we can come back to this theme. But enabling two day delivery for a brand to compete against Amazon takes, you know, a lot of work and a lot of technology to do that. And because people demand their paper towels in 16 hours time after they pressed order. Because of that need that human need and expectation, we now have this huge supply chain conundrum that takes a lot of people in companies to help solve. And I love looking for those companies and pointing back to my fiance who needs something in 12 hours time. I’ve seen that the problem gets solved through the tech. It’s great.
Greg White (20:30):
Yeah. So, to me, I think so much of that speaks to people, right? You talked about technology, you talked about how important that is. But people build the technology. They don’t build it themselves. And guess who they build it for? They build it for people who are going to use it. So, I think it is a fascinating opportunity to see people – to me, I think it’s a great opportunity to see people do something great, to apply themselves, to affecting others in an affirmative way. And so many people say this, “You can go to a thousand pitch competitions anywhere in the world. You don’t even have to go to the valley.” And they want to change the world. Whether they do or they don’t, the wanting to is what’s really inspiring as much as anything.
Greg White (21:24):
But, yeah, you’re right. The key to getting interested in any kind of market is to be excited or at least interested in it. And as you said earlier, supply chain is so complex. It’s not like Asana. It’s not like Salesforce. It’s not like certain things. If you can’t facilitate that e-commerce and facilitate that last mile delivery and everything in between, it doesn’t matter what your brand is. It doesn’t matter what your customer experience is. Because the ultimate customer experience in supply chain is delivering on what you promise.
Greg White (22:13):
And there’s so much that goes into that. And I think even people, regular consumers, you know, put us in our consumer seat, even we understand that as consumers nowadays. Having seen what happened with toilet paper, what happened with Ever Given in the Suez Canal, and all of these other disruptions, the situation in Texas, which is still impacting us and will impact us probably for the next two or three quarters. I can’t get my house painted, Jack, because polymer production went down just long enough in Texas that there is an incredible paint shortage. So, when it starts to hit home, people really realize it. And I think that is the thing that makes supply chain so incredibly valuable is that, it is the business. Supply chain is your main brand equity delivery vehicle. Delivery, no pun intended. But it really is and it has to be, because you have to be able to get the goods to your consumers before you have any need for brand equity. Coca-Cola couldn’t have become Coca-Cola without being able to deliver it.
Jack Freeman (23:37):
Aggravated. And on purpose try to pick embarrassing examples. The first three hours of my morning, I have every single object that I use laid out in a very specific spot so I don’t have to think, clothes, toothbrush, water I’m going to drink. It’s all, like, laid out so that I don’t waste any time moving throughout my day. I don’t have a dresser. I have shelves. Because a dresser would be inefficient. You’d have to open the dresser every time you want to get clothes. So, obviously, I’m not a dresser guy. It looks very much like a factory in my closet. Physical retail, if by choice, if I didn’t go to the store with my fiance to have fun for her, if you ask me, I would order everything online. No, thank you on physical retail. My video is going to freeze. I’m sorry about that.
Greg White (24:37):
I got your back. Do the physical retail part again. We’ll cut that and just do the physical retail part.
Jack Freeman (24:37):
If it keeps freezing, I don’t know – this has happened before. I guess we’ll cut all this. I can go to my phone, but I would suck if it keeps freezing. Physical retail, if it was up to me, I would not do anything in physical retail. Everything could be ordered online. The time to and from Target is an absolute waste of time. Absolute waste of time. I could be doing [inaudible] things –
Greg White (25:11):
You are a natural, Jack. You are a natural in supply chain.
Jack Freeman (25:16):
I’m just getting started. I eat the same breakfast every day. So, similar to like the Zuckerberg thing with his t-shirt, like waste of time to pick out a t-shirt, waste of time to think about what you want to eat for breakfast. Peanut butter toast and fruit every single day. I have a bike, you’ve called out earlier that I started cycling. I do that for a few charities. But if you gave me the choice, I would run versus bike any day of the week because you can run three miles. It takes 20 minutes for me, or 30 minutes, whatever. I get the same workout as an hour long bike ride, in terms of just expenditure. So, the quicker, the better. I listen to my podcast while I brush my teeth.
Greg White (26:08):
This is the best show ever. This is the absolute best. I love it.
Jack Freeman (26:15):
Thank you. And the last one is even a little more crazy. I haven’t been sick in, like, four years. Whenever I do with my health, I don’t get sick. Because going down for three days, as anyone knows, is waste of time. Like, if you go down for three days, that’s the most inefficient three days of your year. So, I don’t get sick, and I’m probably going to jinx myself based on that comment. So, suffice to say, I live my every minute of my life as one big supply chain optimization problem.
Jack Freeman (26:50):
The last thing I’ll say with supply chain, which is more near term or maybe less weird. When I was in college, I did my senior thesis I titled Combinatorial Optimization, which anyone who actually is smart knows what that means to supply chain. Essentially, I took our sports schedule and optimized it for the commissioner. So, you have football, field hockey, women’s soccer, men’s soccer, maybe volleyball, the five main sports in the fall. Twelve teams in the conference, everyone plays ten games, five home, five away. You have to swap home in away with the team that you play every year. You have to minimize the amount of classes that you make students miss. You have to minimize fuel cost and hotels. So, you’ll have to maybe go play Colby-Bates up in Maine in the same weekend. You don’t want to be going from Hamilton to Williams in the same weekend, because that’s a 12 hour drive. All of those variables.
Jack Freeman (27:53):
What fascinates me about supply chain and what I learned at that moment is that, there is no such thing as a fully optimized schedule. The MLB is the best example in a more pronounced way, because there’s 82 games, whatever amount of teams, T.V. slots. As compute power increases, our ability to optimize those equations will increase, but there’s no limit. If the computer power keeps increasing, we’ll keep finding ways to better optimize the scenarios. So, that’s my weird rant on supply chain optimization.
Greg White (28:34):
So, I hope this makes you feel better. But a lot of those things are my traits as well, always eat the same thing. And anyone who’s ever worked with me can embarrassingly quote some of these things. Always went to lunch at 11:30, because I don’t want to wait. If I went out to lunch, I always went to lunch at 11:30 because I don’t want to wait. Waiting in line is a waste of time. I eat the same thing for breakfast every morning. I do use drawers – I have to confess – or doors on my shelves. And I do select my t-shirt each day. But every single day, I’m conscious of the amount of time that I’m wasting selecting the t-shirt. And sometimes I give up and just go Harley t-shirt today, whatever I’ve got.
Greg White (29:27):
So, it’s not as odd as you think. And you will be welcomed and you will probably find more people in the supply chain industry who are like that than, maybe, even in accounting or other industries where you’d expect that.
Jack Freeman (29:46):
I’m thinking there’s going to be some support group that comes out of this.
Greg White (29:50):
Maybe so. And I hope it includes tequila. See, that’s why the tequila.
Jack Freeman (29:56):
Exactly.
Greg White (29:57):
So, my question to you then immediately, Jack, is, if you have all this structure in your day and your schedule and your methodology, how do you deal with disruption? Because that’s the core element of supply chain that eliminates any possibility that a supply chain will be fully optimized ever. So, how do you deal with disruption?
Jack Freeman (30:22):
It’s a great question. I’ll give you an unhelpful answer to supply chain and then a helpful answer. The unhelpful answer is, I think, I started at the beginning of COVID, but I started to do meditation. People can hopefully connect the dots, but just being able to calm down really quick is like a tool to deal with anything, anxiety, frustration. And it’s so hard. Anyone is starting meditation for the first time, like, try counting to ten without thinking about a purple dinosaur.
Greg White (31:00):
Interesting.
Jack Freeman (31:02):
It’s impossible. I promise you, you’ll think of a purple dinosaur the first time you do it. That is number one. The real answer, I think, and I didn’t even think about this as applied to supply chain, but as soon as disruption happens, presence of mind, recalibrate, figure out in the new world that you live in when you’ve been disrupted, what’s the best course going forward. Immediately, there’s new parameters, new variables, new goals, and you level so that you start from square one and move on.
Greg White (31:41):
So, I’ve contemplated this sort of list of things that, I guess, they would apply to life you having relayed that, that I hadn’t thought about for supply chain. So, it’s predict and preempt, plan, it’s monitor, respond, adapt, learn, rinse, and repeat. And, I mean, if you think about that, I hadn’t thought about that. That’s pretty applicable to life. Think about, you know, one of the key things – and, again, not to be too much about me – this is one thing that I think makes someone naturally a supply chain professional is, you think about what could go wrong and you try really hard to prevent or preempt it. You think about what could go wrong in your morning and your ability to get everything you want to get done efficiently. So, you put your toothbrush in the same place, you eat the same thing for breakfast.
Greg White (32:42):
It’s not dissimilar with supply chain, except that for every single one of those things, you have to have a disruptive alternative. What if the cat jumps on the counter and knocks my toothbrush on the floor? What do I do then? Do I have a backup toothbrush? Do I have hydrogen peroxide on the counter – like I do – to clean it if it gets on the floor? What? Anyway, what you’ll find is, supply chain is your support group because they think very much like that. So, you are a natural. So, I have to ask this, did you discover that and then get into supply chain? Did you get into supply chain and then discover the alignment there? Or how did that happen?
Jack Freeman (33:35):
Yeah. It was the latter, which I can explain. To trace my career, I worked at a startup. I think we’re going to talk about that. I worked at an investment bank for a few years and learned about M and A, capital raising, and finance. I then, through that, discovered a passion for working on transactions in a certain stage. So, after investment banking, I got into private equity or venture capital or growth stage. So, through investment banking, I realized partnering with the CEO and a management team and their 30 employees is like the most kickass and exciting time to partner with someone. So, that led me to growth equity. Software to always been an interest. But did not have aspirations to be a supply chain software investor until joining PeakSpan.
Jack Freeman (34:32):
And the way we kind of start is, you start a little bit more generalist. So, if you look at the companies that I worked with, or companies in customer experience management, sales technology, marketing technology, hospitality, through all of that and supply chain, of course, I very quickly gravitated towards supply chain. Probably for the reasons that, “You’re not in your head. You idiot. Listen to yourself.”
Greg White (35:00):
Well, I wasn’t thinking that. But I’m glad that it happened, for sure.
Jack Freeman (35:07):
One, actually, real example, the fourth or fifth partnership that I formed was with a company called Zingle. This goes to your lunch comment. So, Zingle is not a supply chain company. But Zingle is used cases, one that I started to do kind of before they were around, which is, they partner with a lot of location-based businesses, parking garages, delis, restaurants, golf courses, and they do business texting. So, they quite literally have a customer who’s around the corner from my hometown, a bagel store. And they allow the customer to text, “I want a bagel and a coffee,” so that they can come in and it’s ready, not to waste five minutes sitting in line and paying for it and all that. So, I’ve been doing that since I had a phone. I realized, I can call the deli and say, “Hey, can I order this sandwich over the phone?” They’re like, “Yeah. Sure. Whatever.” Order the sandwich, it’s waiting for you when you arrive, pick it up, and save five minutes waiting in the store. That’s what Zingle enabled. And stuff like that really, like, perked my interest right away. And that kind of was a stepping stone.
Greg White (36:23):
And you’re from New York originally?
Jack Freeman (36:26):
New Jersey.
Greg White (36:27):
Okay. But still deli country. So, being prepared, and I’m not sure that the whole world is aware of this, but being prepared when you walk into a deli, especially in New York and New Jersey, absolute necessity. Because the place is – I mean, all the places I ever went in New York, they were always packed, always in a hurry, always maybe a little bit short curt with you. And, man, having that to avoid all of that risk is also a huge benefit, isn’t it? You just walk in, grab the bag and the cup, and walk out.
Jack Freeman (37:03):
Absolutely. If you’ve ever walked into a bagel shop in rush hour – actually, I worked at one when I was in high school. It’s chaos. And, like, having an assembly line and pulling the paper to wrap the bagel in, and scooping the cream cheese, it’s like a show [inaudible].
Greg White (37:28):
I’m thinking of my favorite bagel shop here in Atlanta now, as a matter of fact. I’ll run by New Yorkers, of course, so they already have the incredibly efficient process in place and it is bulletproof process. And you better not try to mess it up either.
Intro/Outro (37:51):
That’s the first half of our interview with Jack Freeman from PeakSpan Capital. Join us next week when we wrap up and you’re going to get to learn a lot more about Jack and combinatorial analytics, maybe even something more interesting. How can I help you improve your shot at supply chain tech success? Four ways. One, subscribe to TECHquila Sunrise wherever you get your podcast to make sure you’re notified of my new episode every week. Two, follow me on LinkedIn and see my supply chain summaries every weekday. Three, if you’re a startup founder or growth stage leader and you need an active advisor to propel you through your supply chain tech journey, I’m currently considering select strategic advisory roles. Or, four, if you need an incubator or investment for your supply chain tech, reach out to me on LinkedIn and let’s talk.
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You Don't Know Jack! Interview with Supply Chain Tech Investor Jack Freeman of PeakSpan Capital
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Jack Freeman has worked with growth-stage technology businesses his whole career and most recently is a partner to twelve portfolio companies at PeakSpan. Prior to joining PeakSpan, Jack worked for Stackpop, an early-stage startup where he was the team’s second business development hire and helped build out a SaaS-based cost management platform to help CTOs and IT teams buy and manage their internet infrastructure. After his startup was disrupted by AWS, Jack joined Macquarie Capital where he spent three years executing software M&A and capital markets transactions. Jack holds a B.A. in Economics from Middlebury College; and prior to Middlebury, he played division I soccer for Seton Hall University. Jack lives in Brooklyn Heights with his Fiancé and recently rescued puppy, Willow – the sweetest Great Pyrenees you’ll ever meet. Once a year, Jack champions a team of thirty in a charity bike ride to the Hamptons to support his brother’s autism program, Quest, where he’s raised over $100K. Jack still tries to hold his own out on the pitch (soccer), but has become a more avid marathon runner and is halfway to completing the “big six” world marathon majors.
At PeakSpan, Jack leads investment theses surrounding Supply Chain, Procurement, E-Commerce Logistics, and Payments. Connect with Jack on LinkedIn.
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