On this episode of The CEO Story, we have Jake Wood. Jake Wood is currently the founder and CEO of Groundswell – a venture-backed software company aiming to democratize philanthropy by building a new category at the intersection of fintech, benefits tech, and charity.


Prior to launching Groundswell, Wood served as the founder and CEO of Team Rubicon, a disaster response organization that is widely considered one of America’s leading nonprofits. Since 2010, Team Rubicon has recruited over 150,000 volunteers and responded to nearly 1,000 disasters and humanitarian crises. Under Wood’s leadership, Team Rubicon scaled to 200 full-time employees across four offices and operated a $55 million P&L. In total, Wood helped raise nearly $300 million for Team Rubicon’s work through a mix of online donor acquisition, family foundations, and corporate partnerships –– to include complex licensing and co-marketing deals. Team Rubicon has become widely recognized for its strong corporate culture, which has been recognized numerous times as the “best place to work in America,” and its technological innovation via partnerships with companies like Microsoft, Twilio, Palantir, and others. Wood remains Team Rubicon’s chairman.

Prior to Team Rubicon, Wood served four years in a Marine Corps scout-sniper unit, leading Marines in combat in Iraq and Afghanistan. He graduated at the top of his class at boot camp, the School of Infantry, and the Marine Scout-Sniper Course. He received three meritorious promotions, with one in combat, and is the recipient of the Navy-Marine Commendation Medal with valor distinguishing device.

Wood is a sought-after thought leader on topics of organizational culture and leadership, frequently speaking at corporate and industry events. Notable corporate clients include Goldman Sachs, Intuit, Farmers Insurance, Travelers Insurance, Facebook, and Carhartt.

Wood’s memoir, Once A Warrior, was an Amazon best-seller and Tom Brokaw stated that “it’s the book America needs right now.”

With weekly podcasts released, “The CEO Story” takes a deep dive into the success and pitfalls of being your own boss! Helping you learn from other people’s mistakes so you don’t have to make them!!

You can find Jake at


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Kc Chohan 0:00

Alright, ladies and gentlemen, we have a peach of an episode for you today. We’ve got Jake Wood from Groundswell.
Jerk is very, very well spoken, guys. Given very, very massive, huge keynotes. He’s been featured in The New York
Times, talked about his journey from being. A warrior to then a nonprofit leader and then an entrepreneur. So
we’re gonna get into those several different stages of his life, how that all evolved and what he makes of it. So,
Jake, thank you so much for joining us. How are you feeling today? Hey, I’m feeling great. Thanks for having me,
Kc Chohan 0:36
Yeah. And you’re looking good to my friends. It’s very good to see you. So. Can you just start by sharing a little
bit about Groundswell, what it is, what you do. And then we can kind of get a little bit more backstory and we’ll
take it from there.
Jake Wood 0:49
Sure. So Groundswell is a venture back software service platform with a goal of democratizing corporate
philanthropy. So at its core, what we do, we provide companies with a platform. That allows them to roll out tax
advantage. Charitable giving accounts to their employees and then give or match funds into them. So guess probably
the best analogy that most of your listeners would understand is it’s like a 401K or an HSA for charity.
Kc Chohan 1:17
Fantastic. So giving back is a very big part of especially the younger generation. I think the millennials
compared to Gen. Y, Gen Z and the Boomers very different in their philosophy. I think a lot of the younger people
want to contribute more, make a difference to the planet. And a big part of that is given. So. What made you
initially come up with the concept and then a beautiful design. It looks very much like an Apple product. When I
was playing around with it, it was very impressed with that. But what was the inspiration behind that?
Jake Wood 1:49
Yeah. Well, I appreciate that we’re really proud of what we built. You know, I think that there’s been.
A groundswell of sentiment among younger generations that companies should exist for more than just maximizing
shareholder values. So, you know, Milton Friedman, you know, famously said that was the sole purpose of any
enterprise was to maximize returns. For shareholders, and. That’s at the root of capitalism. You know, I’m not
here to debate. The bedrock of capitalism. But I do think it’s indisputable that younger folks believe that
companies should have some sort of higher purpose alongside profit, and that they don’t have to be at odds with
one another. They don’t have to be mutually exclusive. So how did I come up with the idea for groundswell. You
know, I have a very atypical background to becoming. A technology entrepreneur. I’m sure we’re going to get into
that. But prior to starting this company, I ran a nonprofit that I’d started back in 2010 called Team Rubicon. And
over the course of about a decade, I raised, you know, almost 300 and 5350 million dollars for philanthropy. So I
really got an understanding of how philanthropy works. What. Works well, what doesn’t. And one of the things I saw
was that companies think they’re really good at giving away money, and they’re not. And I found that to be really
unfortunate, even as good as we were at Team Rubicon at raising money from companies because I felt like they were
leaving so much opportunity on the table. And that opportunity was, you know, better, aligning values with. Their
Really serving to attract values aligned and retain values aligned employees, thereby reducing cost, thereby
ultimately making that corporate flant to be more sustainable. So you know, we really set out with the mission to
decentralize that corporate philanthropy. Empower employees to give that money away.
And you know, the result is 18 months later, we’re out in the market with a really compelling product,
Kc Chohan 3:46
fantastic and a great product. It is as well, because ultimately, you’re making a bigger difference. So you made a
huge difference with Team Rubicon. Like you said, Raisin 350,000,000. It’s a huge number. Right. And that then
goes and becomes very significant for a lot of people. In need so great job on that. But when we look at the
millennial generation of just the younger generation, we don’t necessarily have to tag them with a title. But
people W two employees that can directly give away. It is part of even the advanced structures that we create from
tax savings. But. Really important for people to know that there are options out there and it’s up to 30% of your
top line W two salary that can be donated. Totally tax free people don’t quite realize the power of that. Now I’m
not saying everyone has to go and doing it 30% of their money, but. The way we do it with the high net worth
clients is that if they are W twos usually lawyers and doctors are the ones that fall into the category, but they
can donate directly out of their salary into what we would set up as a private foundation for them so they can do
their philanthropy that way. How does that differ? Or how is it similar to the way you guys do it.
Jake Wood 5:02
It’s funny that you use that. That story of how you work with your high net worth clients. Because I imagine when
you say that. You’re directing that money into a private foundation, which you’re actually meaning is you put it
into a donor advised fund. Is that true?
Kc Chohan 5:15
No. We actually set up the 501 C threes, the private foundations, tax exempt stack. Really? For each of each of
those clients, for the clients that need that specific setup.
Jake Wood 5:25
Yeah. Oh, interesting. So one of the things that I saw was that. Individuals that have, you know, super high net
worth. You know, hundreds of millions of dollars, that’s that’s typically what they do. They set up a 501 C. Three
public charity. Or I was a private public.
Kc Chohan 5:41
Jake Wood 5:42
yeah, or private foundation. It’s slightly different when you get into, hey,
Kc Chohan 5:46
this is for our family. We don’t want it to be in the public eye, but we still want to give that’s why we go
private rather than public.
Jake Wood 5:53
Yeah. And both our options. And I saw them both. And, you know, they both have tons of complexity and tax
requirements and reporting. Requirements Audits All of Minimum Distribution requirements.
But nonetheless, if you have the resources, it’s a good way to go. The the alternative option for just like
marginally high net worth people is you create a donor advised fund, which is effectively a tax advantage
restricted account within a public charity that you can get immediate tax advantages through. But then you retain
advisory privileges over those funds and where they go. And historically, those donoradvised funds have been
inaccessible to the average person. You really actually had to be a high net worth person with you know, somebody
like KC advising you on how you spend your money.
And design your tax strategy. What Groundswell’s done is we’ve actually created the world’s most modern and
accessible donor advised funds. So our platform actually provisions discrete, individual donoradvised funds to
each of those employees. And as a result, makes available to them a giving vehicle that historically they haven’t
had access to with tons of tax advantages. That come with it. You know, they can contribute their own funds and
take an immediate tax deduction without having to give the funds away right away. They can contribute appreciated
stock assets into that not have to pay capital gains taxes. They can invest the balance of those funds for taxfree
growth, for greater giving in the future. And so. That was the approach we took. We kind of took this philosophy
that everybody should be able to give, like, Bill Gates. There’s no reason that they shouldn’t in, you know, 2022.
And that was the that was the vision that we had
Kc Chohan 7:34
it’s slightly different to the way Bill Gates and Warren Buffett. These guys that similar to the way we operate
is. They will create foundations and trusts, and they will donate from one hand give to the other hand. And yes,
they do do a lot of good. I’m not discouraging any of that. But the majority of what they do is still very much
under their control, so they don’t own it. But they control it. So. I really like what you guys. Are doing is very
similar to us. It reminds me of the reason I set that my company together to get four was to take those advanced
strategies that most people don’t have access to and then give it to that. Well, for you, it’s give it to everyone
who’s a W two employee. But for us is to give it to that next level of multiseven to nine figure entrepreneur,
entrepreneur. That’s paying too much in taxes.
Jake Wood 8:24
So, yeah,
Kc Chohan 8:25
very much aligned with that. So continue on the good work. So let’s kind of recap a little bit through your
history because you’ve got a fantastic backstory going from the nonprofit to then. A warrior, and now an
entrepreneur. But again, it’s all back to philanthropy, because what you do ultimately helps give back and make a
real difference in charitable good. What kind of took you into that direction? And can you just kind of take us
through the high level on those different segments of your life?
Jake Wood 8:56
Sure. Why I’ll say that, you know, given back. Has always been a part of my life. I grew up in Iowa, you know,
and. Was involved in the community early on while I was in high school and all of that stuff. Involved in student
hunger drives and things of that nature.
I ended up going to College at the University of Wisconsin. As a football player, I didn’t really think about much
other than trying to get the NFL. Turns out I wasn’t a very good football player. And ended up in the Marine
Kc Chohan 9:24
Jake Wood 9:25
I graduated. I graduated from Wisconsin in 2005. Height of the war. And ended up enlisting in the Marine Corps. I
searched four years there. So, you know, I would say that my commitment to service really accelerated from that
little bug I had while I was in high school. To this notion of serving my country and I served overseas in Iraq
and Afghanistan.
First in an infantry unit, later in a Scout sniper unit.
And honestly, when I got out of the Marine Corn 2009, I kind of thought. My you know my. Era of service was coming
to a close. My plan was to go back to graduate school, get my MBA. Probably go be an investment banker. And wasn’t
thinking twice about that. I ended up accidentally starting a nonprofit in 2010, just 60 days after getting out of
the Marine Corps. You know, again, I was waiting for my grad school applications to come back. An earthquake hit
Haiti. I felt compelled to go. I organized a team to get down there. We got to Haiti about four days after the
earthquake and began running medical triosh clinics all across the city. And, you know, this was this was the
worst humanitarian catastrophe of the last hundred years. It was complete and utter chaos.
And it just snowballed. And if you fast forward from that moment in January, 2010, after the earthquake to today,
Team Rubicon’s got over 1500 volunteers. It’s a raised that $350,000,000 for its work that I mentioned. They’ve
responded to over a thousand. Humanitarian catastrophes and disasters over the over the decade. And really became
one of the I would say Premiere Nonprofits in America. And it was just an incredible opportunity to be an
entrepreneur. But to give back.
And that’s really what led me to Groundswell. I knew I wanted to be an entrepreneur again. I’d gotten the bug, but
I still wanted whatever I did next to be meaningful. And in Groundswell’s really giving me that opportunity. By
again bringing these these donor advised funds and making them accessible to everyone.
Kc Chohan 11:29
No, that makes a huge difference. And can you just explain what the donor advised fund is for the people who don’t
understand what that is. Give them some more context.
Jake Wood 11:39
Yeah? So a donor advised fund. Is a basically a public charity.
Will give donors the opportunity to donate funds to that public charity. And then the public charity basically
serves as a custodian for those funds on behalf of that donor, they technically control it. But what the donor
retains is advisory privileges over those funds. And they can advise effectively, two things. One, they can advise
how those funds are invested while the charity. Maintains them. But then they can advise where the charity
ultimately grants those funds to recipient nonprofit organizations. And so there’s a lot of reasons why.
Individuals use donor advised funds, one they’re just much easier to set up than an actual personal Foundation. We
know the hard work that goes into creating
Kc Chohan 12:31
a private foundation the time. And then, you know, on the IRS side, none of these things move quickly. It takes
about up to a year now because a Corvette being used as an excuse. So definitely. The high net worth people would
look into that. But for the vast majority of people, I would definitely not. I would recommend that they do not do
a private foundation themselves or don’t advise funds is probably the next best thing.
Jake Wood 12:56
Yeah. Absolutely. Because they get they get all the tax advantages. Without any of the headache. And that’s
probably oversimplifying it. But it’s not too far from the truth. And often people will use these because they
might have a big windfall event financial event. That could be that their company goes public. They have a lot of
options. That.
Are certainly suddenly converting. They want to minimize their tax bill in a given year so they may transfer
significant amount of money into a donoradvised fund. Take that full deduction in the current year. But then they
can advise and distribute those funds and subsequent years. And they could be the next year could be over the next
10, 15, 20 years.
And that’s one of the big advantages. And I, of course, mentioned previously that the ability to donate
appreciated assets. And take the full market value of those assets as a writeoff, while not having to pay any
capital gains taxes on it is a huge advantage. And nor does the nonprofit or that in this case, the public
foundation that is serving as the donor advisement. They don’t have to pay the capital gains tax either. So it’s a
winwin across the board.
Kc Chohan 14:07
So yeah. So we can break that down a little bit more because when I tell potential clients that, hey, we can
totally limit capital gains tax the number one. Thing is, how is this even legal? How is it possible? And this is
one where. It works really well for charities. Another way is foundations. Another way is trust. So there’s many
different ways to do this. It’s just how good is your advisory team? How good are the people around you? Because
ultimately the people around you will either know they saw they want. But if they don’t know it, they’re making
you think that it doesn’t even exist. And I think that’s a lot of the problem is. That. Especially with the things
that we do and kind of you’re breaking ground in a whole new Avenue of. A tool for giving and it attacks
advantaged way is that you’re only as good as the team around you. So if someone hadn’t heard of groundswell or
didn’t know that trusts can help you save on taxes as well and control those assets. They wouldn’t know any
better. And we’ve often had conversations with people after they’ve sold a company. Or, like you said, exercise
some shares. I had a big windfall. And they’re like, I wish I’d met you year
Jake Wood 15:20
sooner. All you had to do was research. It like.
Kc Chohan 15:24
Don’t just take the word of your lawyer CPA friend. You’ve got to do the work yourself. And if you’re looking to
give in a charitable way and you are a W two, then ground swell is a perfect way to do that seamlessly designed
and let’s talk a little bit about that because. There’s one thing creating a company and being an entrepreneur.
And then when we start stacking technology on top of that and making technology kind of do a lot of the heavy
lifting. So it’s seamless. And you guys done a great job of that what we’re kind of because it’s a completely
different skill set to be in a standard entrepreneur, because now we’re talking tech, and this is multiple
languages, all within the tech world. And integrations. How did you go about. Building that design and not taking
it from beginning to end and then getting it to work.
Jake Wood 16:14
Yeah. You know I’ve joked with. Our venture capital investors. That everything I needed to learn about being a
software entrepreneur. I learned as a sniper. And, you know, I think. Usually get a chuckle from people with that.
But I really do believe that the foundation of entrepreneurship that I gained was earned in the Marine Corps. When
you think about the work that I did in places like Afghanistan, I worked in a six man Scout sniper team, running.
Operations and missions and some of the most complex and uncertain environments on the planet. And when you think
about what entrepreneurship is.
It’s an impossible mission with you know, typically, what starts as a small team with daunting circumstances, high
stakes, tons of uncertainty and volatility. And there’s only. One option and that’s to win. And so just being able
to navigate risk.
Keep calm under pressure. Exercise good judgment consistently in the absence of perfect information. Those were
the types of environments that I thrived in, and certainly. That’s been the case. First as an entrepreneur in a
nonprofit space and again. I cut my teeth as a nonprofit, entrepreneur. One of the things I learned is it’s a lot
easier to be a for profit entrepreneur than a nonprofit entrepreneur. I went out. I raised $15 million in venture
capital before we even had a product. The advantages that that’s afforded me over the last 18 months and how we
can thoughtfully build a team without having to scrape by for the first five years, like we did a team Rubicon.
I had an investor joke with me once. They said, Jake, you were training with ankle weights on. While you were
running Team Rubicon, if you’ve ever, you know, heard that analogy or used ankle weights in physical training like
you take them off and suddenly feel like you’re the fastest person in the world. And that’s exactly what it felt
like moving over to this.
Kc Chohan 18:07
Fantastic. So I worked with a lot of ex military people. In my corporate job before I sat my own business over at
Florcerv. X Navy people, ex Marines, but mainly X Nuclear people because that’s the subsection I was running. And
the first thing I noticed about the majority of these people was. Their discipline. They were so well drilled.
And, hey, this is how we do it. This is why we do it. Boom, boom, boom? And there was such a big disparity between
a project manager that I was working with, who was exmilitary and a non exmilitary person. And it was like. Holy
smokes. There’s something different about these guys, the way they’re wired, framed, and the way they think so.
Just you sharing that kind of brings back that memory of the old corporate America, but specifically the military
people of the ex military people that I worked with along the way. Just been wired a little bit differently, and
exactly the way you described it, you’ve learned on the hardest battlegrounds in real life, risking your life and
limbs. For the country. And then there’s only one option to win for us all. No one’s in this game to lose. So you
just got to take one step forward every single day, whether that’s a big step or a small step, as long as you go
in the right direction and you don’t give up, you’ll eventually get there.
Jake Wood 19:27
Kc Chohan 19:28
I love that. So yeah. I think you’re absolutely right. You know, that Fortitude, that willingness to persevere,
Jake Wood 19:36
like, perseverance is one of the most important traits that you can have in the Marine Corps. And absolutely one
of the most important traits you can have as entrepreneur.
Kc Chohan 19:43
I was at dinner last night, and we were talking about. Age. I was with a few guys that are a little older than me.
And they were talking about achievements. On one of the guys that just turned 15, he’s like, I don’t feel as if
I’ve achieved much. In my 1st 50 years and I’m like. It doesn’t matter what age you are because you can look at
Colonel Sanders as an example with KFC and many other people that everyone around the table listed to then share
that. You can still become whatever you deem a success is regardless of an age barrier, and the key unifying
factor around the table was not to give up if you give up too soon, if you knock on the first $45 and they say no,
but the 46 one says Yes. If you don’t do those 1st 45, you’re never going to get to that first. Yes. So with every
no, it just gets you closer to that next guess. So definitely perseverance. But I think mindset right. And it’s
definitely linked that discipline, that mindset of winning and achieving what you need to. But doing it in such a
disciplined way, I think that was the one thing that really struck me about the military, people. Are the Xmellary
people? Was that. They were so disciplined. They had their routines. They knew exactly what was wearing. They were
just on top of their shit from a corporate perspective. And I really loved that.
Jake Wood 21:08
Yeah. I think, you know, I’ve had the pleasure of getting to know some nuclear officers.
In pilots are much the same way coming out of the military. I didn’t work closely with either while I was in, but
I’ve worked a lot with them while as I’ve gotten out. And when you’re talking about high stakes, there are a few
things as high stakes as maintaining the nuclear reactor on a submarine five 0ft below the surface of the ocean.
And. One of the things though that I draw distinction on is. Those Nuke officers or call it military. Veterans
writ large. They are very good at doing the simple things really well. And you know, if you can boil those simple
things down into a checklist of, hey, here’s exactly how we run through this process. Yes, they’re going to run
through that process that way every single time. But I think often people put military veterans into a box that
that’s all they’re capable of. Yes, they have discipline, but only in doing things. That they’re told how to do.
But there’s this whole other side of the military, which is more entrepreneurial, which. Does allow for this
empowered creativity for solving complex problems. You know when you think about. Tactics, which is what I just
described versus techniques. Techniques. Is the checklist. Yeah, they’re good at the techniques, but the tactics
is the application. Of everything that they know. Within a novel circumstance. So it’s the application of those
tactics on the battlefield, that judgment in the face of uncertainty. That I don’t think.
They’re often as credited for. But that’s really where you get the entrepreneurs from.
Kc Chohan 22:44
Yeah, it’s kind of strategy, right. So if you did tactics and. Oh, sorry. What’s the second one?
Jake Wood 22:50
Kc Chohan 22:51
techniques, techniques. I would look at the way I frame it is strategy and tactics. One is the strategy of, hey,
what are we going to do? How are we going to do it, then? The second is the tactics that we’re going to use to
execute it. Right. So, yeah, I’m not so aware of that side of the military. Can you give us a couple of examples
of how you were able to kind of.
Accelerate and kind of put your own forever on things whilst serving.
Jake Wood 23:18
Yeah. I mean, I think the battlefield in Iraq and Afghanistan were ever evolving, and it ranged from. You Know,
Troops Finding novel ways to counter. The roadside bomb threat and that might be.
That was both technological. So the US military was constantly fielding new technology on the battlefield to
counter the latest. Ied Improvised Explosive Device Tactics and that range from like.
Cell phone signal jammers to more like blunt instrument, like rollers in front of vehicles that would detonate
bombs out in front of vehicles instead of underneath. Then how troops would implement those things on the
Conversely. Like when I went to Afghanistan as a sniper.
The historical.
Sniper team is a twoperson team, two Marines, a shooter and a spotter. But by the time I got to Afghanistan in
2009, we’d already cycled from a two person team to a four person team. Then we were the first Battalion to field
six person sniper teams on a battlefield. And now you have to understand that the way that. The tactics book had
been written was for a two person team. And now you had to figure out, okay, how do you operate in this threat
environment with six people? It’s fundamentally different. So we wrote that playbook as we were out there for
seven months. And innovated on ways that you could employ six people. In a mission without getting detected. You
know, concentrating fires, all of that to the point where when we got back from Afghanistan, I got pulled along
with three of our other snipers to go to sniper school and teach them the tactics that we had created on the fly
because. That had become the new normal
Kc Chohan 25:07
fantastic. So we can relate that into the business world as well, because that’s a very specific thing, but. That
same scenario happens every single day in business. Where you go into it maybe with a skill set of. Marines or
Finance or Accountant, or whatever your background is. And then you quickly realize when you’re live in player in
the real world, competing with other businesses, then it’s very different. And it’s changing every single day. So
to get over that changing combat, that change you’re reacting in live time, right. If something like Kobe happens
and your business goes completely online versus in person, and now everyone’s panicked and everyone’s going crazy.
But you just figure it out as you go along. I think the key to doing to going through those types of things is
having. Good documentation so systems processes SOPs floor charts whatever your business uses so that you can.
Make the new version of whatever that is. So in this example it was the two person to a four person to a six
person. It may not be six people all around the world at any given time. So now effectively, you can write two new
handbooks, one for a two person team, one for a six person team. Keep that archived, keep it updated. And that’s
the modern way to use. That in business warfare rather than actual physical welfare, right?
Jake Wood 26:30
Yeah. Absolutely. I think.
To build upon that I think one of the dangers that people have in those moments of. Chaos. Like a covet. 19. Right
where they have a playbook. They have the way that it’s always been done. Is, I think weak cultures, weak leaders.
They cling to those things. Those things are valuable, right? They’re the foundation of your business, the
foundation of your operations. But if you cling to them and you don’t realize or appreciate that they were written
for a different world, a different normal. And they may not be applicable in this new normal that you’re
encountering. And if you’re unwilling to. Either evolve them or just shred them and start over.
That could have really dire consequences for your team and so really having that. Understanding. And that courage
to say, okay. These rules. These processes. These systems were built for.
Yesterday. Now, how do we face the threat of today. With the understanding of what we used to do that’s I think
that’s really what separates great organizations from organizations that flounder. In those moments. I
Kc Chohan 27:33
couldn’t agree more. So just to kind of summarize and recap that is to take the knowledge that we already have,
but not. Have it totally be the new Bible and the only way we can do things so use it’s pros but then also don’t
forget to innovate and evolve if the situation or circumstance permits, right? It’s not that it’s set in stone and
we can’t ever change it. We should always be. The way I run my businesses, we should always be trying to improve
everything. And if we can, we need to speak up. But we need to be in a safe environment in order to speak up,
right. I think another part of that is is the culture in the business, allowing the people. Or the leaders. To
speak or not even the leaders. The leader could be the person opening the door versus the CEO. Everyone’s a leader
in their own right. So does the organization. Allow for everyone to contribute. And allow the company to get
better as a whole because if it doesn’t, you’ve got a big culture problem. Yeah?
Jake Wood 28:35
Yeah? And I love the word that you that you used. Do your people feel safe enough to speak up to generate their
ideas, to make recommendations. I think.
All too often when people today leaders today talk about a culture of safety, people think that they’re talking
about a culture of entitlement or coddling people. And I just think that that’s not the case, right? I often I
reflect back on my time in the military. And I always say that the courage that you’d see on the battlefield came
from this sense of safety. And of course, that wasn’t physical safety. Often that courage was in moments of great
physical danger. But the safety was psychological, that safety was emotional because they knew that if they went
down on that battlefield, there’d be a dozen Marines lined up to go and get them. So they felt psychologically and
emotionally safe in those moments of danger. And if, you know, I think if a leader can replicate that. In a
business environment. Where people are not. You know. Kick to the curb for a mistake where people are not.
Chastised for new ideas. But instead they can. They know that they can safely generate those things like that’s
where you get innovation. That’s where you get the right type of risk takers in your organization. Then move it
Kc Chohan 29:51
Yeah. No, I totally agree. And then what are some of the things that you’ve done in your organization to help
curate that culture and empower people to kind of take it to the next level.
Jake Wood 30:04
I always say that, you know, if you’re working backwards from courage, you know, you’ll find safety. But at the
root of all of that is this culture of love, compassion, empathy. And I’m a big believer in that. I think you have
to truly care about the people that you’re leading. You have to demonstrate to them that they are more to you than
just a means to whatever corporate end you’re pursuing. And that means understanding who they are, how they got to
be, where they are today, on your team, you know, pursuing your mission with you. More importantly, where they
want to go in their life, and then convincing them that, hey, I’m gonna be a part of that journey for you. And as
your leader, your manager. Your boss, I’m gonna do everything in my power to make you the best professional
version of yourself, to set you up to accomplish that when you can do that, and there’s a lot of other stuff that
goes into it. But at the root of it, if you can do that. Frankly, you’re 80% of the way there. That’s an
emotionally exhausting form of leadership. You have a lot of people who say, you know what, like I signed up to be
the boss, not to be somebody’s therapist. And I get it. And it is, you know, it is emotionally taxing. But for me,
at least. It is what unlocks.
The most in people.
Kc Chohan 31:15
Yeah, it’s a really good point. And it makes me just think of this one phrase that stairs with me all the time.
It’s be more interested. Than interesting.
Jake Wood 31:26
Kc Chohan 31:26
it’s be more interested in people than you feel that they need to be interested in in you.
Jake Wood 31:33
Kc Chohan 31:33
Jake Wood 31:33
that’s powerful.
Kc Chohan 31:35
It’s the same thing that you’re saying right there is create that environment where people feel loved and cared
for. Because. I’m an accountant so I can talk in account and speak. And the way I phrase it is that people are the
biggest asset of any business yet they don’t appear on any financial statement
Jake Wood 31:53
Kc Chohan 31:54
And it’s without those good people around you.
Nothing gets done. Like, as an example, I’ve got a team around me. And without them, I’m just sat here doing
nothing. It’s like really. And we look out for each other. And it’s like, hey, this is a hole here. This was a
whole hair. And we had to work on what we spoke about earlier, which was.
People being able to speak freely and feel safe, which is why I brought it up because this is a challenge within
my business. It was not everybody was speaking directly to me because their thoughts, oh, my God. Fired. Or this
all that. And I was like, we need to stop this and maybe said this to the team. 50 or so times, but it wasn’t
sinking in. So it was something in my delivery that I had to change. And then when the message kept coming back,
that other people are saying this, and it’s like, Well, why can’t they just say that to me directly, like, that’s
a problem that I need to fix. So eventually. They got to a safety. Threshold. And it’s different for everybody.
But they got to that threshold where slowly but surely they’d have started now saying things more directly, even
though it was nothing really to do with me, because when we got to the bottom of it, it was to do with their own
shyness and their own personality. But more the fact that they’re breaking through those barriers. Of their own.
And growing as people, right. Because ultimately, that’s where the love and affection comes from. They feel loved
and safe. So they’ll start contributing more and growing as a person, which shows up in the business form of, oh,
this person’s actually. Contribute in more ideas to the meaning.
So it’s the knock on consequence of feeling safe and feeling loved that then brings up all this improved
productivity from a business standpoint.
Jake Wood 33:39
Yeah. No doubt about it.
Kc Chohan 33:42
So let’s move forward in the future. So where do you see the future. For groundswell are given because we didn’t
really touch on it. But a lot of these big corporate companies have social responsibility. We had the same thing
at Florcer. When I was there. We had multimillion dollar budget that we had for being socially responsible,
whatever that means. And we wasted a lot of money. So everything that you said really resonate with me brought
back those corporate disk of we’ve got a huge Department. With a massive budget. And nobody really knows what
they’re doing other than one page in the Corporate Financial statement every year that we’re looking at. And we’re
like. What is this really far,
Jake Wood 34:23
so, yeah,
Kc Chohan 34:24
the fact that you brought that up really. Touched on because Floor serves not the only party in 500 companies
that’s like that they all have a percentage of what they give. Are you going into those companies and educating
their Department so they can then let their employees know that this is available and we can integrate it into
ADP. Or like whatever payroll software they use, or how is it? How can the average employee listening.
Get onto ground swell and get their company on board.
Jake Wood 34:56
Yeah. We said a couple things. They’re the really resonated with me. The first one is, you know, a lot of these
CSR departments, corporate social responsibility departments have massive budgets. And I think a lot of people are
wondering. What are we doing with that? And the truth of the matter is often, you know, those CSR efforts are
really just the pet projects of CEOs. The CEO says here’s what I think is most important. And we’re gonna do this.
Sometimes they’re right. Sometimes they’re wrong. But the truth of the matter is if you got a thousand employees.
And you have only one person making a decision about what the most important problem is to try to solve or what
the best solution is to fund that’s not representative of what those thousand people care about. And so our
argument is. Maximize the impact of your CSR by celebrating the diverse perspectives of your people. You know, you
and I. Listen, if we work at the same company, what you care about socially, the issues that matter. Most of you
are going to be wildly different than they what matters to me. So why are we having one person in these companies
make that decision? Just doesn’t make sense. And so you know, our approach. Is we’re not you know what’s called a
product lead growth company. We’re not coming in through.
Rank and File Employees We’re selling software. To Enterprise buyers. And that means we’re going primarily to
human resource departments. And executives within those HR teams. To sell this as a corporate benefit. So what can
listeners do if they’re an employee at a company and they want to take the ground swell away.
Send a note to their head of HR and say, hey, you know, how can we. Decentralize or democratize our corporate
philanthropy and give me a piece of it, right? Give me a piece of where we send this in ground soul is the way to
do that.
Kc Chohan 36:42
Yeah, because there’s a lot of advantage. And just to recap to the people listening, if you are an employee of a
company. And you want to take some of those tax advantages because you get a big benefit as well. You get to
potentially control where that money goes, how it’s invested. But you also get a tax deduction in the given year
that you do that. So it’s not just all about given. That is some personal gain in there as well. So everybody
wins. It’s a winwin. All round. And ultimately, that money can go to good. I do a lot of philanthropy myself. I
have my own Foundation. We’ve recently done a lot for sex traffic children
Jake Wood 37:19
in La specifically over the age of 18 because the system stops caring for them at age 18 and put some back onto
the streets. And they
Kc Chohan 37:28
tend to go back into what they know best. So we’re trying to support that and trying
Jake Wood 37:33
to, well, keep
Kc Chohan 37:34
that breast. It’s ridiculous. The numbers of people that actually fall into these categories that we just don’t
realize. We’ve been working with Donna Pearson and the Russian tech group on that. So that’s very close and dear
to my heart at this moment. But any type of given norm matter how big or small it is, it all makes different. So
with that is the central focus, whether it’s. Tax advantages, whether it’s just donor advise funds. So you
literally can control where that money is spent. But it doesn’t even have to be that it could be as simple as
going to your local charity or religious place and helping out. It doesn’t even have to be financial. It’s just
trying to make the world a better place. So with that being said J. Jack, what are the best ways for people to
contact you? I’ll reach out to the company and kind of get involved.
Jake Wood 38:24
Yeah, well, I’m pretty easy to find personally, I’m pretty active on LinkedIn and Twitter so people can find me.
You know Jake Wood, just Jake would adjwood Tr on Twitter. Backslash JakeWood USA on LinkedIn.
The website for Groundswell’s WW Groundswell IO. You can get in touch with us there. Reach out for a demo. You can
also follow grounds while across all the social channels. Again pretty easy to find We’d love to have you started
dialogue. And see where it leads.
Kc Chohan 38:57
Great. Thank you so much for your time. And for everyone listening, we’re gonna put the links right down below
here for Jake and Ground swell as well. So you mix life easy for you, Jake. Thank you so much for your time.
Jake Wood 39:07
Yeah. Thanks for having me. It’s a great conversation

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