Jessica Willis: Founder And CEO Of Pocketnest

MJH 8 | Financial Literacy


In this episode, we sit down with Jessica Willis, the founder and CEO of Pocketnest, to learn more about her entrepreneurial journey in the financial literacy space. Jessica shares valuable insights on the most common financial mistakes young people make and offers practical advice on how to avoid them. She also offers her experience and tips on capital raising, an essential aspect of building a successful startup. Jessica also talks about the financial challenges as a parent on both sides of the spectrum, and discusses the sweet spot between parenting and money. She emphasizes the importance of finding your community and building a good culture around your cap table. Join us as we dive into the world of financial literacy and entrepreneurship with Jessica Willis.

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Jessica Willis: Founder And CEO Of Pocketnest

Welcome, Founder and CEO of Pocketnest, Jessica Willis. Thank you for joining.

I’m happy to be here, David.

A lot of entrepreneurs talk about that light bulb moment when they first get the idea of a startup. Did that happen to you, or was it something that happened gradually over time?

It was a little bit of both. That might be part of my nature, which is a little bit of a Midwest conservative. It took me a few years to leave my super stable, safe, and high-paying job with 3 kids and 3 mouths to feed, and a husband. I had the moment of, “Why doesn’t this exist?” I did a lot of diligence to make sure I wasn’t missing something for that first year. I had the idea and was watching what robo-advisors did and, to me, they were pretty siloed on the investment side. They brilliantly figured out how to bring investment to the masses, but I couldn’t understand why there wasn’t something similar addressing estate planning, income tax planning, saving for kids’ college, and all the things that keep us up at night.

I found a lot of FinTechs doing those things siloed, but the piece that I saw missing was why isn’t there something that knows everything about somebody that can give advice into all those different segments? There was a moment of, “Why doesn’t this exist?” after a few years of talking to everybody who would sit down and talk with me to understand that there was a niche or a need for what we were doing, so a little bit of both.


MJH 8 | Financial Literacy


As an entrepreneur, I’d probably have ten ideas a day. Sometimes a simple Google search is like, “Somebody’s already doing that.” It does make sense. You don’t have to test the waters with both feet. You can test it with a toe and get more confidence as you get more information. Since you’re in the financial literacy space, what are the most common financial mistakes young people make, and how can they avoid those mistakes?

There are a couple. I’m going to classify them by age groups. When you say young people, the first mistake all humans make is we don’t start saving early enough. Anytime I talk to someone in college or graduating college, the moment you get that first job, you’re going to get a bigger paycheck than you’ve ever received in your life, and it’s going to feel like an obscene amount of money at the time. It’s better to start building the habit of socking some of that away then versus playing catch-up later. Phase one of life, graduating college, that’s the first mistake. Get into the habit of maxing out your 401(k), not only to get to the match but even as much as you possibly can, and then start socking away and building that habit of saving.



The second stage of life is parenthood. When individuals start having children, we feel like there are a million things we need to do for estate planning, how to teach your children good financial habits, how much life insurance you need, and how you start saving for college for them while paying down your own student debt. There are all these things. It’s one of those life-changing events when the finance stuff hits the fan.

The mistake that I see over and over is that we become paralyzed and don’t do anything. “I don’t know how to talk to my kids about money, so I’m going to wait until I can figure out how to do it perfectly. I don’t know how much we need in insurance, so I’m not going to deal with it right now.” I see it in the markets too. People are not feeling like they know exactly how to start investing in the capital markets, so they step back and wait. As you mentioned, getting your toes wet. I love to encourage people to get their toes wet and start.

The wealthiest I’ve ever felt in my whole life is when you do get that first job. You’re like, “OMG. $26,000 a year, what am I going to do with it?”

You look back as a more grown adult and realize how little you had. That’s why it’s so much easier to push yourself to save then.

You look back as a more grown adult and realize how little you had. That's why it's so much easier to push yourself to save then. Click To Tweet

You also think, “If I can only make this, I would never have to worry about money again.” When you get there, you’re like, “No. Forget about having kids, mortgages, and all of that fun stuff.”

That goalpost keeps changing.

I’ve heard that it’s hard to be a parent financially when you don’t have a lot of money because you always have to say no to your child for things, but also when you have a lot of money, you also have to force yourself to say no, not because it’s easy to give things. On both sides of the spectrum, it can be difficult.

I’ve seen a lot of that. I’ve been an advisor, wealth manager, and CFP for twenty years. I have dealt with a lot of different people on this socioeconomic spectrum. There is a sweet spot for parenting and money. I’ve seen when individuals don’t say no because they have so much that leads to all sorts of problems for children and third generation, specifically. On the other end of the spectrum, we always want to give our kids what we didn’t have. I do think there’s a sweet spot in the middle.



I was speaking with a friend who’s a Goldman Sachs wealth management advisor. I said, “What do high net worth people worry about the most when it comes to their money?” He’s like, “How do I not have my kids turn out to be jerks?” It’s fascinating to hear that.

I could not agree more.

What’s been the toughest part of your entrepreneurial journey thus far?

After taking the leap because that was the first thing that was tough, I would classify it as we don’t know what we don’t know. The advice around that is don’t be afraid to acknowledge that you don’t know what you don’t know because there is a universe out there that’s dying to help you. I’ve seen founders love to help other founders. People who have gone through building and exiting a startup are willing to help advisors.


MJH 8 | Financial Literacy


It’s recognizing that there’s this fine line between nobody has ever built Pocketnest before, so nobody knows exactly what the right thing to do is, but you also don’t want to spin your wheels constantly. There are people out there who have figured out and have valuable advice on how to raise capital, hire a CTO, build a team, and all these things. It’s getting that balance right between recognizing you don’t know what you don’t know and seeking help, but at the end of the day, you still know what’s best for your own company. That can be challenging.

I agree. There’s that saying, “Fake it until you make it,” but if you fake it, nobody knows you need help. If nobody knows you need help, then you’re not going to get that help. I’ve found the entrepreneurial community, especially as you mentioned, the people that have exited companies, while they can buy what they want, they miss being part of that energy and excitement. They want to help and want to pass the advice and all the potholes you can avoid. They’re so willing to help which I’ve found in this amazing community.

That’s the first advice I give to startup founders when they say like, “What do I do?” It’s not building a deck or getting investment. It’s finding your community. You have to find your community and define that however you want. You have to have a community in the startup ecosystem locally and nationally. For us, it’s the Midwest. Find that community to support you because you cannot do this on an island. It’s impossible.

MJH 8 | Financial Literacy
Financial Literacy: It’s not building a deck or getting investment. You have to find your community and define it however you want.


On that note, congratulations on your funding round. It has gotten a lot tougher than it was before. There are a lot of startups that are struggling to raise money. What advice would you give in terms of raising money?

There is so much. Thinking back to the paralysis thing, just start if you haven’t done a fundraiser before, but also be very methodical about it. There’s some formula to raising capital. Call me and I’ll talk you through that a little bit more, but it’s not just going out and start asking people for money. That certainly isn’t it. Get a little bit methodical about how much you want to raise and who are you targeting. Do the preliminary work, and when you’re ready, go. I do worry about macroeconomic trends over the next twelve months. We’ve gotten ourselves into a position and raised enough for 24 months runway.

I recommend that we all try to build that runway for whatever’s coming down in the next 12 to 24 months. Have fun with it. One more thing is we look at raising capital as, “I have to raise capital.” It’s a full-time job, but like anything in life, you’ve got to have fun with it. If you’re not enjoying having the conversation with the investor you are talking to, you’re probably not going to be fit. Bless them and release and move on to someone who gets what you’re doing and find those people to support you.

MJH 8 | Financial Literacy
Financial Literacy: Raising capital is a full-time job. But like anything in life, you’ve got to have fun with it. If you’re not enjoying having the conversation with the investor you are talking to, you’re probably not going to be fit.


I say this all the time. People talk about culture as it relates to employees and everything. I also think it’s important to have a good culture of your cap table. Surround yourselves with people that you want to work with. A lot of investors want ROI on their investment, but they also want to come along for the journey and all the benefits with that. Being in the Midwest, did you have to go to the coast, or were you able to find capital in your neighborhood?

Yes, everywhere. You talked about cap table culture. We have a healthy cap table culture. Every one of our investors I talk to with some frequency, even if it’s like the attaboy text here and there of them saying, “I loved your newsletter. Keep going,” there is not a single investor on our cap table that I don’t adore. I can call them at any moment with any questions. That’s important.

Before we were looking at, “Where do we raise from?” we were looking for, “I don’t want to work with jerks. How do we find the right people who we want to work with?” We got capital from all over. There’s a lot going on in the Detroit startup ecosystem. There’s some capital from there. Also, from the Midwest. We’ve got investors from New York, California, and Boston.

You find your people wherever they are. It’s interesting that over the last couple of years, we’ve had COVID, which has eliminated the need to fly out to the coast to have a fifteen-minute meeting with an investor to meet them so that they know you for your next round. That’s ridiculous. I love that we’ve been able to meet and find the yays and the nays pretty quickly and efficiently over Zoom calls. It’s been wonderful.

Capital has been democratized in the last several years. It used to be all venture capital. Now, you have family offices, corporations, individuals, and angel investors. It’s not easier to get, but it’s not monopolized, which is pretty cool.

You get to find your fit a little bit more. We’ve got a mutual connection through a credit union that’s an investor. Before we started, we chatted about how great they are. Again, you have to look for your culture fit.

Unlike venture capital, as we mentioned with our mutual investors and credit unions, they become partners as well. It’s a double win. Not only are you getting capital to grow, but you’re also getting a partner, which is great. I always like to end with a question about you personally. It’s always different depending on the person. For you, what personality traits are you most proud of that you think are unique to you and have shown throughout this process?

I chatted about it with my husband and a couple of close friends along the way, but it’s what I call, ” Okay, and.” I’m a rule follower. I want to know what the rules are my whole life like, “Tell me the rules. Great, I’ll follow those,” but I always feel like there’s this like, “Okay, and,” that goes along with it. This is the way things are usually done. Something that I’ve always been able to do is like, “I understand that, but, or, and how do we make it work in this world?”

I’m a single founder. I didn’t have that technical cofounder. I’ve been in wealth management. I took one coding bootcamp that was horrendous for me, and it’s not a fit. I knew I was not going to build the platform. I kept hearing in those early days when I had the idea, “You need to find that technical cofounder.” My response was always like, “Okay, and I don’t have that technical cofounder right now. I’m not going to sit on my hands for the next few years until I find that person. How do we go despite that?”

“The statistic shows that only 2% of capital goes to female founders.” “Okay, and how do we keep going despite that?” I don’t know technically what that’s called, but that’s something that has always helped push me along. I understand how things need to be done, but how can we also morph that into something that works for everybody? It doesn’t have to be it works or it doesn’t work. There’s something in the middle of those two things.

It’s important to understand how things need to be done. But you also need to figure out how to morph that into something that works for everybody. It doesn't have to be “it works, or it doesn't”. There's something in the middle of those two things. Click To Tweet

“There’s the well-paved path that everyone takes, but what about this one on the right that’s less paved? I’m not the first person in history that started a successful company without a technical cofounder. There has to be a way.”

In the earliest days, we had an opportunity for a huge customer that didn’t end up panning out, but it was a huge opportunity. I remember calling an attorney. It’s not the attorney I’m working with now. He was trying to mentor a little bit, and he is like, “No, you can’t do it.” I remember being like, “I’m not going to walk away from this deal. How do we do that while doing this?” I must have talked to him for five calls back and forth over a few days. Finally, I realized, “You’re not going to be the attorney that’s going to help get us all the way there.” We found a way around it, and the deal didn’t end up panning out, but you can’t walk away from opportunity.

I could not agree more. I always say have yes attorneys. If no is clear, can we find a way for a yes? That’s what I’m looking for. It’s going to take work.


MJH 8 | Financial Literacy


You have to ask the question with the how. You can’t say like, “Can we do this?” It’s, “How can we do this?”

That’s a great answer. Jessica, this has been great. Hopefully, everyone has learned a little bit about you and your journey. If anyone has questions, please feel free to LinkedIn, Jessica Willis. She is part of a family of similar investors that we have. I’m going to be rooting her on, but thank you for joining me.

David, thank you. It’s so nice to meet you. I appreciate it.


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About Jessica Willis

MJH 8 | Financial LiteracyJessica Willis, Founder & CEO, PocketNest – Jessica has spent nearly 20 years of her career in the investment and finance industries and has obtained the Certified Financial Planner (CFP) and Certified Private Wealth Advisor (CPWA) designations. Jessica has an MBA from Loyola University Chicago, Quinlan School of Business and a B.S. from University of Michigan. Jessica has a passion for serving individuals, getting messy financial plans in order and a love of smart fintech tools that improve efficiency and accessibility. Offline, Jessica loves spending time with her three children and husband, Tom.

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