Jake Wood, Founder and CEO of Groundswell, on Putting Philanthropic Giving in the Hands of Employees

David Folwell: Hello, everyone. Thank you for joining us for another episode of The Staffing Show. Today I am super excited to be joined by a really close friend and amazing entrepreneur, Jake Wood, who is the founder and CEO of Groundswell. Jake, to kick things off, why don’t you do a little introduction on who you are? And then just give us a little background.

Jake Wood: Yeah, sure, Dave, always good to see you. My second time on the show, so excited to be back. I think the first time I was wearing a founder and CEO of Team Rubicon hat. So good to be back for the second act here, yeah. I mean background, and Dave mentioned we’re good friends, we went to high school together. Interestingly, had a pretty entrepreneurial class out there in Pleasant Valley, Iowa. Been a social entrepreneur for the last decade and a half. I started a nonprofit organization called Team Rubicon in 2010 after serving in the Marine Corps. That scaled pretty dramatically over the last decade plus. That was a disaster response, humanitarian relief organization, mobilizing veterans to do that work. Today it has about 150,000 volunteers. And I think I’d be remiss if I didn’t add that as Hurricane Ian is slamming into Florida, Team Rubicon has boots on the ground all over the state, ready to assist, doing great work.

But decided to be an entrepreneur again. And 18 months ago, I stepped out of the day-to-day role there at Team Rubicon. Started Groundswell, which Dave mentioned, is a software company. So not exactly a direct line from the Marine Corps to disaster response, to fintech, venture-backed fintech company. But I saw an opportunity in the corporate giving space to build a platform, to really level up how companies do their philanthropy and more specifically how they empower their employees and the diverse perspectives of their employees to do that philanthropy on their behalf. So really excited. We raised about $15 million last year led by Google Ventures in a seed round. Launched the product earlier this year, came out of beta in May. We’re hooking and jabbing, trying to sell into companies across the country right now. And really excited to be building a team again, starting from scratch and trying to have that second-round success.

Folwell: That’s awesome. And also just add that Jake is an Amazon bestseller with the book Once a Warrior. He has been a TEDx speaker, built successful organization with Team Rubicon. But I know most of the time for all of our audience, most of the people that we have on this podcast are really in the staffing industry, heavily focused on the staffing industry. So today’s going to be a little bit different. We’re going to be talking about a broader range of topics. First, we’re going to talk about how corporate giving can increase employee engagement and retention. We’re going to dig into Groundswell and talk about what Jake’s doing on that front. Next we’re going to dig into leadership and just talk about what you can do to build and lead a team effectively, since Jake has a lot of experience in that front. And then we’re going to jump into the importance of your company vision and mission. With that, we’re going to kick it off. Let’s jump into Groundswell. So why did you start Groundswell? What was the foundation for this?

Wood: Yeah, when I was running Team Rubicon, I raised about $300 million in philanthropy. So I raised money from all sorts of sources, ranging from Fortune 100 companies to billionaire family offices and tens of thousands of regular folks all across the country. And I think I learned probably a couple of really important lessons. One, it always bothered me that normal people didn’t have access to the same giving tools that really rich people had. And that ranged from, either tax advantage vehicles that they gave out of, the philanthropic advisors that they surrounded themselves with, the strategies that they were able to pay for and have produced. And I just felt like that wasn’t fair and that playing field needed to be leveled. And the second thing is, companies give away a lot of money and they’re really bad at it.

And some of them, most of them in fact, don’t admit that they’re bad at it. And I just felt like there was an opportunity for them to take that same philanthropy, have better impact in the communities that they were trying to support, and drive better business outcomes by inspiring and motivating their employees with it. So we developed this idea for Groundswell, a B2B SaaS platform that creates personal giving accounts for each employees and then allows companies to gift or match funds into those accounts, that the employees can then give away. And what the employee does is they download an app, it’s a donor-advised fund. It’s kind of a technical tax-advantaged vehicle that historically, only ultra-rich people have had access to. And so it’s really truly made an employee benefit. It’s made philanthropy a component of compensation.

So knowing that this is a staffing show, I would argue that this is highly relevant. The companies across the country today are in a fierce talent war. They are competing for the best people. They’re competing to keep their best people. And in doing so, they’re competing on compensation, they’re expanding their benefits offerings, they’re trying to build a culture that attracts and retains people. And one thing I think we’ve learned over the last 18 months is you could only compete on compensation for so long. And compensation across some industries have gone through the roof. And at a certain point, you have to differentiate yourself. Second, I think a lot of folks now know that millennial and Gen Z talent make up the largest share of the workforce and they want to give back. It’s well documented, they want their companies to have purpose alongside profit. Frankly, Dave, you and I, we’re geriatric millennials, we’re at the upper band of that.

Folwell: Yeah. Yes, we are. The elder millennial, yeah.

Wood: And I don’t think anybody actually knows what that means, purpose alongside profits, it’s somewhat squishy. But I think that the companies that figure it out, are going to be the ones that consistently win for that top talent. And so our argument is, “Hey, the easiest way to align corporate values with those millennial and Gen Z values is to just simply empower them to give that money away.” 74% of Americans are donating to charity every year. That’s more than the percentage of Americans that are contributing to a retirement account. So when you think about…hey, I’m not saying that’s a good thing, it’s….

Folwell: That’s amazing stuff.

Wood: … it’s just something about the psyche the population. But it’s pretty fascinating. And so you can provide a meaningful financial benefit to your people by subsidizing their charitable giving. And the win that creates and really that values alignment between employer and employee is powerful. So I would argue, and frankly, this is our whole go-to-market strategy, is this is not corporate philanthropy. This is an HR benefit. This is an opportunity to rethink total rewards and total compensation for a new generation.

Folwell: That’s interesting. And so in terms of how it works, normally a company, I mean, I think about corporate philanthropy and corporate giving, typically it’s the company’s choosing an organization. They’re saying, “All right, we’re going to give all of our money to this organization.” And there’s people that work at that company that are probably, some of them are like, “That’s great.” And there’s others that are like, “That’s not where I would’ve put my money.” And if I understand this correctly, are you basically saying, “Instead of just giving away this lump sum to one organization, say we’re donating X number of dollars, but we’re going to let you as the employee allocate that,” is that….

Wood: So that’s certainly a part of what the product does. So I think, again, I mentioned Hurricane Ian earlier. So let’s talk about what’s happening right now. Three million people out of power in total devastation, untold number of people missing right now. You have a lot of CEOs that are sitting in a boardroom today saying, “Hey, we’re going to give a million dollars.” And that CEO’s probably saying, “Let’s give that million dollars to the Red Cross or World Central Kitchen or Team Rubicon.” And I’ll never argue against giving it to Team….

Folwell: I mean always Team Rubicon.

Wood: But let’s think about this for a second, through the lens of DEI, what does that CEO probably look like? Probably pale, male, and stale, old white guy. So his decision process for where that money goes is through the lens that he views the world. Maybe he’s a really smart guy, and he makes the right decision. But when you have, and you hinted at this, your employees might be proud that the company’s given away a million dollars, but they’re probably also saying, “I would’ve given it somewhere else.” Because if you are a first-generation American immigrant, you might be saying to yourself, “Wow, this is going to really impact Hispanic communities on the Florida coast who maybe English is a second language, and I’m going to support an organization that’s been working exclusively in marginalized BIPOC communities.” Or, if you’re a single mother, you might look at this through the lens of, “Hey, I’m going to support a local shelter on the ground focused on battered women.”

If you’re an animal lover, you might be thinking about all the dogs that are left behind, the cats that are left behind as people are evacuating. And you’re going to support a no-kill animal shelter. So by empowering your people, and you’re exactly right, you basically take that million dollars and if you have say 1,000 employees, you deposit $1,000 into their Groundswell account and you say, “Hey, go support however you want.” Ten different organizations, 100 dollars each one, 1,000 bucks, whatever it is. And for us, we think that ultimately there’s wisdom in the crowd. You’re going to get money to smaller organizations that may otherwise be overlooked. You’re still going to have a lot of that money flow to big organizations like Team Rubicon that are going to do tremendous work on the ground and need large volume of cash. And you have this huge win in that empowerment and that acknowledgement of the diverse perspectives of your people.

Folwell: That’s incredible. And the one area that you’ve talked about and you’ve touched on just a little bit, and I’d love to understand more, is how is this a tax advantage? And you said that it’s a tax advantage that the all too wealthy have had and used. How does this impact employees? How does this impact the company? How does that work?

Wood: So again, employees get this account called a donor-advised fund. And think of it like an HSA for charity. If a company puts money into an employee’s Groundswell account, the company takes the tax write-off as a charitable donation. But employees can contribute their own funds, the platform enables matches. So if, you know, Dave, if you had an account and you worked for a company, you put $500 of your own money into it, and your company had a match, like an HSA or a 401(k), then that match would automatically go into your Groundswell account. You’d have $1,000 to give away then.

And then you get the tax write-off for your amount, the company gets the tax write-off for the amount they put in. But the interesting thing about donor-advised funds is that tax deduction happens immediately, even if the money’s not immediately sent to that recipient charity. So that means that you can donate money in this fiscal year, maybe on December 31st, take a tax write-off for 2022, but distribute those funds across charities in 2023 and beyond. So huge advantages there. It allows you to contribute appreciated stock into them and not have to pay capital gains taxes, all sorts of things. Again, this is how rich people give money away, and we’ve brought it to everybody.

Folwell: So you’re basically saying we’re going to give that away, let’s save that, and then choose that a later point and save tax on it because of that.

Wood: Yeah, so let’s use a scenario, like if you’re working at a major tech company and it’s about to go….

Folwell: Yeah.

Wood: … you have a ton of stock options, you could transfer some of your stock options that have massive appreciation into a donor-advised fund, it might be millions of dollars. You take the full write-off of the value of those stock options. You’re not paying capital gains taxes on them and you’re reducing your taxable income in that year. And you may not know where you want to go give away that million dollars that you just put in there. You’re like, “I got to develop the strategy.” But you can take that tax write-off immediately. So again, there’s a reason rich people have been using these things. That’s why we wanted to make them accessible to everybody else.

Folwell: Oh, that’s really cool. And honestly, that hits the nerve, even for our organization, when we’ve done donations at the end of the year, we get basically everybody in the group, “Who do you want it to go to?” Everybody’s voting on it, and then it never aligns. Everybody has a different cause that they want to support. So this is really cool overall. What type of companies are you working with right now? Who should be considering looking into Groundswell?

Wood: Yeah, so we’re working with a lot of tech companies right now and professional service firms. So think investment management firms, like hedge funds, private equity, even some VC firms that aren’t even our investors, accounting, law. Right now it’s really a trying to approach mostly white-collar industries where there’s high, medium levels of education, relatively high revenue per head, just kind of makes it an easier sell. Ultimately, we want to see this as an accessible tool for every industry across the country.

Folwell: Yeah, I love that. And what do you think the impact of Groundswell could be on nonprofits? And you mentioned that it’s going to go to smaller nonprofits and that it’s probably going to broaden it out. But do you have any idea what the overall impact could be?

Wood: Yeah, I think one, it’s our intent, our vision for the mobile app, where the employee is distributing their funds is to create better data, collect better data, help with that data present better, more algorithmically driven recommendations to users. I mean, there’s a lot of people that want to be more philanthropic. They see things happening, and they say, they might pass a homeless person on their way to work one day and say, “Man, I’d really love to support that issue, but I don’t know the first thing about it.” And so that moment between inspiration and action has too much friction, and the result is they don’t take action. We want to be able to say, “Hey, we know you’re in Denver, you just search for homelessness. We have the ability to surface for you the organizations that are most suited for that.”

The second thing is having run a non-profit, with traditional corporate giving programs, there’s a massive lag in when that donation match comes in. So again, think about right now with Hurricane Ian, there’s going to be a bunch of companies that are saying, “Hey, we’ll match up to $500 if you donate to Team Rubicon.” And so these employees are donating to Team Rubicon, then they’re having to submit that receipt to HR, and then it goes to accounts payable. And literally 60, 90 days from now we’ll get thousands of paper checks coming in from these companies, which is the company’s portion of that match. We don’t even know this money’s coming, we’re not even tracking. It means that….

Folwell: So it’s not even impacting the actual moment, like right now, you don’t have the cash today to do what you need to do, yeah.

Wood: And we can’t even begin to spend it yet.

Folwell: Because you don’t know.

Wood: … you don’t know it’s coming. So that just massive implications for numbers.

Folwell: That’s interesting. I’ve never even thought about that gap, and that happens all the time, where companies are like, “Hey, we’re all donating for this,” and you think you’re helping the cause, but the reality is that that money’s coming so late that you’re helping the next one.

Wood: Exactly, and so the money’s not going to go to waste. But the number of times we were responding to a major event, and we’d say, “Okay, based off early fundraising velocity, we estimate we’re going to raise $2 million.” So that’s our planning factor as we plan operations for the next 45 days. Well, if we knew we had an extra million dollars, the planning factor changes fundamentally, and you’re either planning for more aggressive action in those 45 days, or you’re already planning for 60 days. So it’s a big pain in the ass for a nonprofit.

Folwell: The, that’s really cool. One other area that you talked about, and I don’t know if you have stats on this yet because I know you’re in the startup phase, but the impact on employee engagement and retention. Obviously, from my perspective, I can see how it’s just awesome. It’s like I’m going to be able to choose where I want to put the money, feel like the company’s aligning with my objectives and what I care about. But do you have any stats that back that up or any use cases from current customers?

Wood: Yes. One of the interesting things that I think we’re helping companies with is there’s no shortage of these, I call them moments of social upheaval. Let’s rewind the clock, even just two years, you had first COVID, and then you had George Floyd get murdered, you had multiple black men that same summer, Breonna Taylor getting murdered by police, then you have Stop Asian Hate. And then Israel and Palestine flared up, and so antisemitism became a thing, and it hasn’t stopped, right?

Folwell: Yeah.

Wood: That was just one summer, two summers ago. Now you have Roe v. Wade getting overturned. You have all of these things, and each of those moments are the most important moment in at least one of your employees’ lives. And they are expecting you to take action on it. So the number of emails that CEOs get, HR leaders get now, “Hey, what are we going to do about X, Y, Z issue?” is overwhelming. And frankly, responding to them is pretty unsustainable.

And so a lot of our companies see this as, I don’t want to sound trite, but almost like an escape valve for that, because now it’s less, “Hey, we have to make this centralized decision,” and more, “Hey, we’ve empowered you to take action in this moment through your Groundswell account. And so this is how we are engaging on this issue.” And I think that that’s a really powerful opportunity. And at least CEOs breathe the sigh of relief when we talk them through what that can do for them. The other interesting thing is it serves as a leading indicator for those issues because you’ll get data in real time via your administrator dashboard of what your people actually care about. So if you see this event unfolding and you’re like, “Man, I wonder if this is the one that we should”….

Folwell: Oh, that’s cool. Yeah, that’s interesting.

Wood: Yeah, look at the data. Are your people pouring money into that issue? If they are, yeah, you better get out in front of it. If they’re not, that one squeaky wheel is demanding action, that person probably isn’t even donating to it because…. So it’s some fascinating use cases there.

Folwell: I’ve never thought about that. There’s like a strategic HR component of making sure you understand what your employees want and that you’re moving in the right direction and aligned with them. That’s really cool. With that, let’s jump over to the next section of this interview. When it comes to leadership, clearly you’ve figured out a lot of things. You’ve figured how to grow organizations. What are some of the things that you learned about leadership from the Marine Corps?

Wood: The Marine Corps set really tremendous foundation for me for leadership. But I’ll tell you man, I get out of the Marine Corps, and I became a CEO, and I realized I still didn’t know anything about leadership. And some days I wake up, today, 12 years on as an entrepreneur and CEO, and I realize I don’t know anything about leadership. So definitely, one of the things the Marine Corps taught was just this notion of uncompromising leadership. Like you, from a personal vantage point, that level of self-accountability, demanding excellence of yourself. One of the tenets of Marine Corps officer training is it’s above the door when you enter Marine Corps, The Basic School, is what it’s called TBS, is “Know thyself and seek improvement.”

And I think that that notion of you have an obligation to the people you’re leading to be the absolute best leader within the organization. The absolute best tactician, the absolute best you name it. And so just that relentless accountability of self is, I think, really, really powerful. I think the military is really well known for them just taking care of its people. This leadership notion of “leaders eat last.” Simon Sinek went to a Marine Corps whatever training and was blown away by this idea of leaders eat last. Which frankly, sometimes Simon Sinek sees things and is blown away. And I’m like, “That seems pretty simple, Simon.” But I think leadership, excellence is in the basics. It is things like that. It’s taking care of others before taking care of self.

And I think if you can do that consistently, people will look to you, they’ll be inspired by you, they’ll be willing to follow you because they know that leadership for you is selfless. It’s about others, it’s not about self. And I think see a lot of founders who build companies and it’s about themselves, and that’s always very transparent. And I think that those founders, they can build effective companies. If they’re brilliant and highly technical and can raise money, they’ll build successful companies. They won’t necessarily have the best teams. Again, if they’re brilliant enough, they could overcome it. I’m not that brilliant, so I’m only going to be successful if I build a good team. And I think the easiest way to do that is to convince people that you’re in it for them. And that’s just the lens I always think about it through.

Folwell: I think that’s great advice. And with that, in terms of how you’ve gotten to be the leader that you are today, are there resources, books, courses, any other tips that you would suggest for the audience?

Wood: I’ve always tried to surround myself with amazing leaders. So I think leadership’s a contact sport. You’ve got to get out there, you got to lead. You learn to lead by leading. And you learn to lead by following great leaders. You learn to lead by leading great leaders. One of the things that early, at Team Rubicon, the temptation for any young entrepreneur, young founder, first-time founder, is to hire people that are noticeably less talented than them because they’re concerned, they’re….

Folwell: With their ego.

Wood: Sometimes it’s ego, sometimes I think it’s fear. I think it’s self-doubt, if this person’s super talented, will they follow me? And I think, I don’t know, maybe we fell into it, but we hired some people that were just incredible leaders themselves early, that I could learn from every day. It forced me to become a more humble leader. I don’t think many people look at me or interact with me, and I’m not sure humility is the first word that comes to mind, but I do actually think it’s why….

Folwell: I think it’s a strength.

Wood: I think the people who really know me, who work with me on a daily basis, they know it because I’m the first person to admit that I don’t know the answer to something. And I’m the first person to push the right person forward in a moment and say, “Hey, we’re behind you in this moment.” And I think that served me well. I don’t know if it’s a universal leadership trait or not, but it certainly has served me well to be humble enough to know when I’m not the right person for any particular task.

Folwell: Yeah, absolutely. And one thing that you’ve also done is the teams you built have obviously been excellent. I think in one of our previous conversations, you talked about how you really love strategic HR and thinking about who do you need and what skills do you need? Any advice on how to select the top talent or even just on HR strategy as a whole?

Wood: Yeah, I mean, you’re right. I might be the only software entrepreneur in history whose second hire was an HR leader. I swear to you guys, I hired a chief product officer here at Groundswell, my second hire was my former head of people at Team Rubicon.

Folwell: Really?

Wood: Yeah.

Folwell: That’s amazing, I didn’t know that.

Wood: And she was one of my ride-or-die partners with Rubicon. Helped me scale the people and culture there. And going back to what we were just talking about, I knew that if we’re going to be successful at Groundswell, it’s going to be because we hire the right people, and we can’t afford to get it wrong out of the gate. So we invested in that early. Again, you won’t see that at many places.

Folwell: It makes sense because when you get the right person, it changes everything, absolutely everything. When you have the right person in the right role, it’s wild, so.

Wood: The smartest move I ever made, and she’s about to go out on maternity leave in a month and a half, and I’m f-ing terrified. But listen, I think hiring great people, everybody says the same thing. I think you got to hire for culture. We always talked about “passion trumps talent, but culture’s king.” I’d rather have someone that’s super passionate than someone that’s super technical or experienced. And then lastly, passion doesn’t always translate into culture fit. And so you have to hire for that first and foremost. Now, none of those things are mutually exclusive, and you should be able to find super-talented people that are good culture fits.

But in the absence of it, you got to hire for that culture. And listen, at the end of the day, there’s a lot of talk these days on diversity and diverse teams. I think we didn’t get that right early at Team Rubicon, and it took us a while to really unwind that. And as a result, it took us a while to unlock the power that those diverse perspectives bring. And I can’t say why we didn’t get it right early at Team Rubicon, it just, I guess, wasn’t a focus, wasn’t something that we emphasized. But I think we’re doing a great job here at Groundswell. We’re getting incredible talent from people that just have the craziest backgrounds and experiences, many of them atypical. And I think it’s created a really rich environment and pretty low ego, which is always good.

Folwell: That’s the best. I feel like working with people that can admit when they’re wrong and challenge each other. It’s critical for early stage and probably the whole path. With that, I just want to touch a little bit on, you actually spoke at our Staffing Hub Live! conference a few years ago. A lot on vision and mission and the importance of that. Could you just share a little bit of your thoughts on that?

Wood: Yeah, yeah. I talk about those types of things pretty frequently. Any leader, anybody who’s ever led knows that their first responsibility is establishing vision for their teams. And I think most leaders probably understand the building blocks of that. I kind of break it down into three things. Vision’s got to be pretty simple. It’s got to be bold, and it’s got to be relatable. And by simple, I mean it can’t use ambiguous language. It’s got to be very clear, very concise, no ambiguity, bold. A vision is meant to inspire. If it’s not bold, who’s going to be moved by it? And then it’s got to be relatable. People have to hear it, understand how their effort, their work, their blood, sweat, and tears moves the needle towards accomplishing that. But to be completely frank, creating a simple, bold, and relatable vision is really easy. It’s not hard.

It’s like, hey, we want to be the best boutique staffing agency in Denver area for c-level talent in the tech industry. It’s like, “Boom, I nailed it!” But I mean, the hardest part about vision setting is not the crafting of it, it’s the execution of it. Because if you actually expect it to do something, to inspire people, to serve as their north star, then the hard part is, as leaders, making sure that after communicating it, you align every single action and decision and resource to it. You can’t cut corners. The moment that your people see a disconnect between what you say you want to do and then what you’re willing to do to get there, it loses all power. And so that’s what I always challenge people with is like, hey, if you’re not willing to put in the effort to be the best staffing agency in the state of Colorado, then tone it down and say like, “Hey, it’s Denver.” Because there’s a difference there. It has to match your ambition, and then your ambition has to match your inputs, your blood, sweat, and tears.

Folwell: Yeah, and I’ve actually got a question with that is you can always say, “I’m going to be the best staffing agency in Colorado.” How do you make sure it actually aligns with what your team wants? How do you make sure that that’s something that’s actually exciting? Because that’s a gap that I think I see a lot of people struggle with is like, “All right, well yeah, we want to be the biggest, best, but do people actually care about that?” And when it’s like people care more about the corporate giving or they care more about tying it back to doing good in the world versus just being the top. And that’s, I think, a gap that a lot of companies struggle with.

Wood: I think there’s two ways to approach that question, which is I think a really good question to ask. The first is, well the team isn’t inspired by it, get a different team, right?

Folwell: Yeah.

Wood: And I don’t say that with any bad just intent, but it’s your company, right?

Folwell: Yeah.

Wood: If this is the direction you want to take it and people aren’t getting on board, it’s time to make changes. But if it is that collective effort and you’re trying to pull people around and rally around something, yeah, you better understand what’s going to motivate and inspire them. And so it’s interesting that you say that because the example I always use in talking about visions is Southwest Airlines and their vision has, from the beginning to be the most flown, most profitable, and most loved airline in the United States. And the operative word there is most loved. And the way I always frame this with audiences is like, “Which airline wouldn’t want to be the most loved? You think United and American and Delta are saying like, ‘Uh-uh, we don’t care if people like us.’”

They want it, but the reality is the only airline that consistently makes decisions, takes actions, sets strategy around the idea of that consumer sentiment, and some of these are really hard decisions that impact seemingly, the bottom line, like not charging change fees, no check bag fees, all of that stuff. They’ve made those in pursuit of being the most loved, with the expectation that our employees are going to be more happy because they’re not dealing with angry customers. We’re going to let them have fun on the flights, which is just a crazy experience. United flights where they hate their lives to a Southwest flight where they seemingly actually enjoy their job. And they have the foresight to realize that if we can do that, the profits will follow. But again, when they set that vision, it wasn’t an easy decision then to go and not charge change bag fee or check bag fees and do all these other things that customers hate. So it’s easy to say you want to be the most loved, it’s really hard to then actually go out and do it.

Folwell: Yeah, I think that’s a great point. I mean, I see a lot of people, I mean most corporate visions that I’ve participated in, companies I’ve worked at, you see it, you read it, you laugh about it, you’re like, “Okay, I see every single day, I see every one of these rules being broken.” People aren’t following this, the buy-in is the key part there. So with that, we’re going to go jump into the final part of the interview. So I’ve got some personal questions for you. What is the advice that you wish you were given before becoming an entrepreneur?

Wood: Get better dental insurance. So for me, stress manifests with clenching my jaw. And I’ve broken like five teeth with clenching. And so I’ve had to get crowns on, all my molars are crowned now from just clenching. And early on, I’m not kidding, I was paying out of pocket for that stuff.

Folwell: You got a grind guard now?

Wood: I do, I don’t wear it because I’m an idiot. I think people glamorize entrepreneurship and listen, it’s the best decision I ever made. I’d do it all over again. But make no mistake, if you do it right, if you are actually an entrepreneur with ambition, you’re not trying to build a lifestyle business. And there’s nothing wrong with lifestyle business, sometimes I wish I had one. But if you’re trying to do something that’s truly going to change the game, it’s going to be a grind, it’s going to be miserable. You’re going to wake up every day wondering, “Why the hell am I doing this to myself?” But by the time the night comes around, you’re like, “Oh man, that was great. I had such a good day.” And then you’re going to do it all over again the next day.

Folwell: Love it. In the last five years, what new belief, behavior, or habit has most improved your life?

Wood: In the last five years? Wait, you know what? I would say, maybe this isn’t the question you asked, but my daughter turned four today. My oldest daughter, I’ve got two daughters. My older one turned four, and I saw somebody write a tweet, tweeted something the other day. I’ve never met this guy, I follow him. I think he’s pretty interesting guy. And he wrote, “Fatherhood is the only thing in life that ever lived up to the hype.” And I was like, man, that is so true. There’s so many things people talk about it, “Oh, this experience is incredible, this, that, getting here, doing this is the best thing you’ll ever do.” Yeah, some of them are pretty cool, but everybody hypes up fatherhood or having a child, and you would think, “Oh man, there’s got to be a letdown in there.” It’s the only thing in my life that has ever actually fully lived up to the hype.

Folwell: That’s incredible, that’s great. What is the book or books you’ve given most as a gift and why?

Wood: Mine.

Folwell: I was going to say, I think I know the answer to this one. Once a Warrior.

Wood: Yeah, Once….

Folwell: How about number two or three?

Wood: Yeah, number two. So I don’t do that often, but when I do, it’s been a book that was really special to my dad that I didn’t appreciate until he passed away. And I actually found a copy of it in his desk drawer. And it’s called The Go-Getter, it’s 100 years old, it’s 50 pages long. And it’s just this quick story about a guy who comes back from World War I missing an arm and goes to work for a business owner in his hometown, a lumber mill guy. And the guy sends him on this impossible task and literally impossible because he told him to go get this blue vase that didn’t exist. But the guy moved, come hell or high water, found a blue vase. And the moral of the story is there’s two types of people in this world, and you want to be a go-getter. And so I actually have two blue vases up here on my cabinet that….

Folwell: That’s awesome.

Wood: … were my dad’s. But every once in a while, if I need to think about going the extra mile, I’ll just go look at the blue vase. 

Folwell: I love it. How has a failure or apparent failure set you up for later success?

Wood: I think my life has been a series of failures, truly. I don’t say that in a self-deprecating way. I went to college to play football, I turned out to be a terrible football player. I went into the Marine Corps, I lost the Marines that served underneath me, I lost Marines when we came home. My first software startup was a complete failure. I got fired from my first job after the Marine Corps, which is a story I almost never tell. And I think that what I’ve learned is that yeah, you’re going to get punched in the face in life, and you just got to clench your jaw and keep going. And those failures, I got a lot of battle scars from them, and they’re great. They made me who I am. So I celebrate those failures and vow never to do them ever again.

Folwell: Awesome, awesome. And last question I’ve got for you is what is an unusual habit or an absurd thing that you love?

Wood: Waking up early and starting my work day. I typically get up between 4:30 and 5:00 AM.

Folwell: We’re on the same schedule these days.

Wood: Yeah, yeah, and I just start working. I love being able to work quietly. Usually, I do my Wordle before I start work.

Folwell: You start every day with a Wordle?

Wood: Yeah, usually.

Folwell: All right.

Wood: I crush it.

Folwell: I imagine, I imagine.

Wood: It surprises most people that I’m up at my desk at 4:30 in the morning.

Folwell: So with that, any closing comments? Any last things that you’d like to share with the audience?

Wood: No, knowing again, that there are staffing experts and professionals out there, just an interesting anecdotal story. I was in a meeting with the CEO of a major company, the CEO of a major advertising conglomerate in New York and his chief people officer. And I was pitching him Groundswell. And I’m five minutes into the pitch, and he says, “Jake, stop.” I’m like, “What do you mean?” He’s like, “We’re going to do it. We’re going to buy it. We’re going to implement it. I love it.” And I go, “This is amazing. You barely know what we do.” He’s like, “No, no, no. Let me tell you a story.” He said, “Three years ago, one of our biggest competitors was recruiting me, and they put an offer in front of me for a lot more money.” He said, “I went back to my company here, the board, and they matched it.” He goes, “And then I was in a dilemma because I was really considering going to this other company.

So I go to my mentor and I asked my mentor what I should do, and he said, ‘Hey so-and-so, you really love supporting that one charity that you’re involved with. Why don’t you go back to both companies and ask them to put 100,000 dollars into a donor-advised fund, so that you can give it to this charity and based off how they react, you know your answer.'” So we went back to both of them. The one company that was trying to recruit him said, “Why the hell would we do that? Why don’t we just give you an extra 100,000 dollars?” And the company that he was currently at said, “We think that that’s an amazing request, and we would gladly do that for you.” And so he stayed with who he was with, and he got 100,000 dollars. And so I would leave you with that story as you think about what can move the needle in placing some of that talent. These are the types of things that matter to a lot of people. And just keep it under consideration as you’re out there recruiting or placing people.

Folwell: Awesome. Well, Jake, thanks so much for all of the insight. Thanks for joining me today. I really enjoyed the conversation.

Wood: Yeah, thanks for having me again.