In short
Founder exits and why traditional wealth management outreach happens after the highest-stakes decisions are already made; what should replace it (earlier, trust-based planning built around “math, tribe, compass, growth”); how AI may reduce back/middle-office costs but humans remain essential for emotional optimization and relationship.
Guests (backgrounds)
- Stephanie Kirkpatrick: Founder of Pretty Smart Money; former founder/CEO of Orem; longtime certified financial planner; principal inventor/patent holder for a financial advice patent; previously in financial advice/wealth management (15+ years).
- Kate Moody: Customer Strategy Director at 11FS; works in ventures/consulting with banks and fintechs to design customer-focused financial products.
Key claims
- Wealth management is too narrow (portfolio/AUM) and too late (after liquidity/exit decisions).
- Advisors get paid in ways that bias them toward assets under management and cold outreach.
- Founders often miss critical planning windows (e.g., QSBS/83(b) election, prenups, debt/401k decisions) due to lack of education and access.
- Trust comes from relationship and context, not commissions or “shiny” offers.
Notable examples
Catcalled inbox after raising $85M; founders missing QSBS/83(b) window; first-generation immigrant founder unsure how much she owns after SAFE notes; debt payoff example where “progress” can outweigh pure math.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOGuest Introductions and Backgrounds
0:56 to 3:06
Introduction of guests Stephanie Kirkpatrick and Kate Moody, discussing their backgrounds.
“First up, we have Stephanie Kirkpatrick, who is the founder of Pretty Smart Money and Orem.”
The Journey of Exiting a Business
3:06 to 4:53
Discussion on the emotional complexities and decisions surrounding business exits.
“I'd love to talk a little bit more about the periods surrounding Orem joining Stripe.”
Identity and Transition After an Exit
4:53 to 7:58
Exploring the identity shift and challenges faced after selling a company.
“fraught with a lot of complex decisions.”
Wealth Management's Timely Arrival
7:58 to 12:30
Stephanie shares her frustration with wealth managers reaching out post-exit.
“You only really know what's missing sometimes when you sort of get to a place and have a thing that you, I work really hard to get to a role that after having I realized I didn't want.”
Critique of Wealth Management Practices
12:30 to 14:00
Discussion on outdated practices in wealth management and the need for relationship-building.
“And thinking about the operators who are in tech who have the same challenges that the founders often do.”
Understanding Wealth Management Flaws
14:00 to 19:18
Learn about the shortcomings of current wealth management services and their impact on entrepreneurs.
“But lots and lots of people, our entrepreneurs, our builders, have kind of those inherent desires to go and build things.”
The Emotional Journey of Founders
19:18 to 26:50
Explore the emotional challenges founders face in financial decision-making and the importance of proper guidance.
“Did they do any predetermination of if this doesn't work out and I was the sole owner of the company or a substantial shareholder?”
Reframing Wealth Management Perspectives
28:00 to 31:18
Explore how wealth management should encompass broader financial decision-making criteria.
“But income streams and various income streams, not just a salary, but other ways to generate income are as meaningful as potentially building up your wealth portfolio.”
The Role of Personal Support Systems
31:18 to 34:04
Discuss the importance of social and familial support in financial decision-making.
“I mean, as you say, that's a decision-making criteria rather than a financial instrument in that sense.”
Social Media's Influence on Financial Advice
34:04 to 37:08
Analyze how social media shapes the way people seek financial advice today.
“Well, I think, Kate, you point out something so different in today's version of social media.”
Show all 17 chapters
Challenges in Traditional Financial Services
37:08 to 39:48
Examine the shortcomings of traditional financial services in providing meaningful advice.
“We're living in a world where, as you say, video content can be so heavily personalized to each individual, but actually still it's a random dude on LinkedIn reaching out.”
AI's Potential Impact on Financial Advice
39:48 to 42:01
Discuss how AI could revolutionize financial advice and the importance of human touch.
“Yeah, I guess on the point of making money, I mean, definitely we've seen weird things happening in the market lately, haven't we?”
The Importance of Progress in Financial Decisions
42:01 to 43:29
Explore how making small financial progress can motivate better decision-making.
“I know that I should pay off this high interest rate card first, but the student loan debt that I've had for a decade is embarrassing, makes me feel bad every time I look at the balance.”
The Role of AI and Human Interaction in Wealth Management
43:30 to 45:20
Discuss the balance between AI optimization and the need for human advisors in financial services.
“coming in to really optimize with agents, that middle and back office.”
Future Predictions for Financial Services
45:21 to 47:22
Anticipate the evolution of financial services over the next five years with AI integration.
“it changes the context of financial services again, doesn't it?”
The Shift Towards Family-Centric Financial Planning
47:23 to 51:00
Learn about the trend towards focusing financial services on family units rather than individuals.
“Five years from now, obviously Steph by then, pretty smart money is going to be ridiculously successful as well.”
Wrap-Up and Key Takeaways
51:01 to 51:58
Summarize key insights from the discussion on future financial advice.
“So on that note, we better wrap up this discussion.”
Transcript
Automatic transcript. May contain errors.0:14David Brear:David Brear and today we are talking about one of the biggest moments in a founder's journey, an exit. For many entrepreneurs, selling a business is seen as the finishing line. But in reality, it's the start of a completely new set of financial decisions. Suddenly, there are questions around tax, investing, planning, family, purpose. And if you're anything like today's guest, a flood of unsolicited emails from wealth managers you've never met before. Weird, huh? So why does financial advice often arrive at the biggest decisions that have actually already been made? And if we were designing wealth management today, would it look anything like the industry we have now?
0:53David Brear:That's what we're going to be exploring on today's episode. And to discuss this, we are joined by some super-duper awesome guests. First up, we have Stephanie Kirkpatrick, who is the founder of Pretty Smart Money and Orem. Hey, Steph, how are you doing? Hey, David. Good morning. I'm doing great. Thanks for having me. For anybody that doesn't know you, do you want to give yourself a bit of a background? Absolutely. Hello, everybody. I'm Steph. I'm the former founder and CEO of Orem and a longtime certified financial planner. Actually, over 15 years of the time I've spent building in tech companies, most of that time was spent not in payments, which is where Orem was born, but actually in financial advice and wealth management.
1:31I'm the principal inventor and patent holder for a financial advice patent. And so I'm just uniquely, I think, interested in this category of financial advice and the world of wealth management. And for today, specifically, why is it so weird to have people reach out to you and want to talk to you about money when they've never actually met you. So it's going to be a really fun conversation.
1:52David Brear:Sounds great and lovely to have you on. We have also been joined by Kate Moody, who is the Customer Strategy Director at 11FS. Kate, I'm pretty sure everybody knows you at this stage, but for anybody who doesn't, do you want to remind them what you do at 11FS? Yes, I wear two hats. So one of those hats is getting to meet great people like Steph on the podcast, like today, and the other is working in our ventures team. So the consulting side of our business at 11FS, where we partner directly with banks, fintechs, anybody that wants to build and design new products and services in the world of financial services and money, just try and make things work better for customers.
2:25So yeah, I'm a self-certified customer nerd. So just love really trying to understand those customer jobs to be done, like what those unmet customer needs are and really think about how we connect those into better products and services. So yeah, I'm really just excited to learn from Steph and her experience today as well.
2:39David Brear:Very cool. I feel like we actually need to make those hats for you, Kate. Like, you know, I feel like we could do it quite literally with FinTech Insider or 11FS swag, couldn't we? I wouldn't say no. I do have a very large head, like literally not, hopefully not metaphorically, but they'd need to be quite substantial heads. Yeah, you meant literally not egotistically. You're actually very, you know, down to earth, aren't you? Fingers crossed. We'll find out. All right, guys, let's dive in. Steph, before we get into your LinkedIn post that really sort of spurred all of the reasons while we're here.
3:10David Brear:I'd love to talk a little bit more about the periods surrounding Orem joining Stripe. It must be quite a weird feeling when those things happen and, you know, the acquisition itself and, you know, leading a company you've started and run for a period of time through that type of exit. I mean, what was the experience like? Is it what you always thought it would be or is there anything unexpected? You know, this is part of the founder journey that I think doesn't get a lot of conversation. We talk about building, we talk about the goal to have an outcome, And then nothing else. There's like very little written, spoken, talked about.
3:44So I'm so glad you're asking this question. I have a little bit of a unique experience because I went through an acquisition when I was a part of the management team at LearnVest in 2015. We were acquired by Northwestern Mutual. So I had a version of what it might feel like in my head, but I wasn't the founder. And when you're in the founder seat, you're facing, honestly, the highest stakes financial decision you've ever made in your life. And not only are you having to think about those decisions that might affect your own future, you have to think about your shareholders, your customers, your employees.
4:14So there's a really complex puzzle to put together when you're trying to find the right combination of where to land the company ultimately. And I think, you know, one of the reasons why I find this moment so under-discussed is because truthfully, very few people are in your corner when you have to make these choices. and you suddenly start to realize that what might be best for your board and your biggest institutional investors might not be best for your customers or your employees. And so there's just a ton to navigate. And as founders, if we're doing our job right, we always say like the hardest things are to come.
4:51And I think this is one of those moments that certainly for me was ambiguous, emotional, fraught with a lot of complex decisions. And that's just leading into getting it done. And there's a whole bunch of other complexities that are on the other side, most of them emotional, at least for me, but certainly one of the most complex things I've been through in my entire career.
5:11David Brear:Yeah, I can imagine it's sort of an exercise in sort of rationality and the feeling of irrationality. You know, your business is your baby sometimes, isn't it, when you're sort of putting everything into it and making those things happen. And, you know, the trust of people who work there and, you know, the people who you're sort of entrusting them into, that must be quite. And I should say as well, I mean, I've seen founders sell to gigantic banks and, you know, their culture be sort of, you know, reasonably assimilated in not a positive way. But with somebody like Stripe, you know, we've had people like Patrick Collinson on the podcast before.
5:49David Brear:He's a gigantic believer in culture of businesses and structure and those things. But that must have played a big part in finding somebody that was, you know, worthy, I mean, in the nicest possible way. but to take that all and move it forward. Yeah, absolutely. The fit is a part of the conversation. And I think, you know, having worked at Stripe, it's such an important part of my career. And still, I find myself surprised a little bit by this identity shift. And this, you know, I write about this a lot. In fact, I posted about this last week that once you're no longer the founder, no matter how fantastic the company, no matter how amazing the culture, no matter what big work you're working on, you suddenly have to rethink even like how do you stop and introduce yourself?
6:38Because for a long time, your name, title, logo, and founder is a big part of that combination. And then you have this identity shift. And for me, it's lonely. I say to people often, it's easy to stay busy after all is said and done. It is harder to feel like you truly belong to something in the way you did when you're in the build. I think it's probably why founders repeat the journey because no part of it is easy, but parts of it are so compelling and emotionally connected that once you've been through it, you've yearned for it again. And I've had to give myself real coaching to say, don't dive in too soon.
7:19But there are just myriad problems that as a creative builder mindset, you're attracted to. Coupled with the fact that there are, you know, I think tremendous points of influence from outside your day-to-day life, investors who backed you before that want to back you again. And so finding the right balance between, you know, settling with what's just happened, re-identifying yourself, remembering that there's more to you than being a founder, which has been a good part of the journey for me. And then thinking about what is next? And is next necessarily a venture-backed company or is next something that's super high impact?
7:57And maybe more purpose, you know, that transition from high ambition to purpose and meaning is something that I spend a lot of time in this kind of second chapter thinking about.
8:08David Brear:It's interesting, isn't it? You only really know what's missing sometimes when you sort of get to a place and have a thing that you, I work really hard to get to a role that after having I realized I didn't want. And actually, it's quite a weird feeling that, isn't it? It is. You know, it's not a waste. It's finding what you value most and the things that, you know, get you springing out of bed every day to, you know, to march towards solving, isn't it? And that's different for everybody in that sense as well, isn't it? It really is. And I mean, this was seven years of my life where the good, the bad, you're surrounded by a team.
8:47You have people to go rally every day. There are customers who need you. And then one day that ends. and you might still have meetings on your calendar and super important things to do, but you really have to kind of rethink who am I if not a founder? And that's been unusual and unexpected for me.
9:03David Brear:I feel like there's a previous founders sort of forum. It's like a self-help group. We need to get people together to talk about this one. But we'll come back to that, I think, in a later episode, though, because I think it's a great thing to unpack and explore because, as you say, there's not a lot of people who have gone through that in a repeated way. And it takes a certain type of person to like that type of pressure and structure and everything that goes with it. But one thing that I guess, you know, clearly stood out was with everything that happened with the announcement and the things and what sort of brought us to have this podcast was you shared on LinkedIn that your inbox was suddenly filled with wealth managers offering to help.
9:47David Brear:You sort of described it like being catcalled, which I'll be honest, I found funny. And I think I actually laughed out loud when I read that one. But what made that experience so frustrating then? Because it's a strange one, isn't it? I bet it sort of felt like, you know, friends, only friends because of the success, essentially, which makes you sort of question everything really, doesn't it? Well, it's so true. Only friends because of the success is kind of a feeling. And actually just backing up for a second, prior to writing this post, whenever I had fundraising news, people that I barely knew from high school or incidental contacts would show up in my life, net jets would send me emails.
10:29So there's like definitely points where I'm sure other founders would tell you that, you know, the more newsworthy you are, the more you hear from people that perhaps you weren't interested in hearing from. In this particular case, having come from a financial planning background myself and knowing really deeply how the industry works. On the one hand, I wasn't surprised. On the other hand, I was like just grossed out, you know, because first of all, I think, I wonder, did you not think I was worthy of talking to before? Why not build a relationship when you saw I had raised$85 million and that I might be on a path to have an outcome leader?
11:09Why not build a relationship around all the equity decisions and complex tax questions, right? There are many moments in a founder's life, some of which are public, thanks to the way fundraising news works and public filings and other things, that would suggest that you could get to know me before the chapter closes instead of coming to look and having that sort of low trust moment. And I was flooded. Name brand advisors, name brand firms, Goldman Sachs, Morgan Stanley, UBS, right? Top of the house, you know, big wealth management teams. And they are persistent, right? Offers to get flown on a jet somewhere.
11:50Invites to 11 Madison Park for dinner. Like, all kinds of things. Shiny. And maybe for some people that works. But for me, this just doesn't land in a place where I feel like I am gaining trust with someone. it made me feel like, I think catcall was the exact word, right? Like attractive and interesting for the wrong reasons. And so I hope that by building pretty smart money and starting to rethink how this all works for an industry that hasn't changed in decades, that there's a path to actually doing this right for other people and helping founders, not after they've made some of the hardest decisions, but actually before.
12:30David Brear:Yeah. And thinking about the operators who are in tech who have the same challenges that the founders often do. Well, like you say, if they would have been potentially useful on helping you achieve these things, you might have something of a relationship in order to talk to them. But I always find it quite funny, you know, it's referred to as a liquidity event in this instance, isn't it? That, you know, most people at Pi Net Worth or Ultra Net Worth have gone through some sort of liquidity event, which I'll be honest with you, I think it makes it sound like you wet yourself. Like it's not a, it's not something that I think is like should be an aspiration, you know what I mean?
13:02David Brear:but definitely you shouldn't only try and make friends with people after a liquidity event. That doesn't make any sense either. But, okay, I mean, it feels like the wrong way around, right? You know, people should add value in order to earn trust to then be able to help people when they're useful, not just wait until they're successful and then try and acquire them as a customer, right? No, I was just thinking, listening to Steph, I think two of the kind of biggest problems in the wealth management space, certainly as I see them at least, seems to come through really clear, First and foremost, I think there's a really outdated idea that when people have liquidity events or acquire wealth in whatever shape or form that takes you, that that's kind of them done and dusted.
13:42Like suddenly you've kind of reached this tier of financial aspiration and you just want to stay there. Whereas actually, I think what Steph described is much more the experience that I've had when I've spoken to people that are managing portfolios of different kinds. Like some people do just want to sit with that money and keep it secure and maintain a lifestyle. But lots and lots of people, our entrepreneurs, our builders, have kind of those inherent desires to go and build things. And I think a lot of the current wealth management services don't recognize that. They just kind of want to manage the money.
14:13They don't want to help the person that is connected to that money to feel fulfilled, to have opportunities to continue to build and grow, whether that's financial or personal. and then yeah the other part of it which I think came through very clearly and what Steph was describing which again we've seen time and time again in our research is that too many of these organizations are still orientated around like monetizing customers in the wrong ways you know as Steph was sort of saying people just pop up from the woodwork when there's you know a big event and they can see oh I can make this commission on this transfer or this They're not thinking holistically about how do I build a relationship over the longer term?
14:54And maybe that means you have to think about where you make your money as a wealth manager differently. You need to be able to connect with the customers earlier on. So I think a lot of the perceptions about what people want to do with their wealth are wrong. And a lot of the ways in which wealth managers are planning to make money from the people they serve are wrong. And these are fundamentally combining to create really poor outcomes for people like Steph.
15:17David Brear:Yeah, it's a strange one. We've sort of been through these things in various different guises, Steph, and it's an interesting one. So you must have experienced it as well. And obviously, I think it's particularly a weird one when somebody who's worked in financial services for a period of time, so know how to do these things to a certain degree, you get treated like you're a child, sort of. It's a really weird structure. It's almost like it's like the random LinkedIn DM that nobody's looked at anybody's background to understand what they know. It's like, it's just very bizarre, isn't it? But I mean, one of the things that you actually said, Steph, was the biggest financial decisions happen before an exit.
16:01David Brear:But it's long before, isn't it? You know, it's not a, to your point on the structure of equity or all of the things that you're doing or, you know, understanding why you're doing all of these things in the first place. It's not a financial transaction. It's the outcome of serious intent for years and years, isn't it? So just unpack that a little bit more because I think, I feel like we're telling basically coots how to do their job at this stage in the UK, but it isn't just them. It's all of them, isn't it? I think they all have similar patterns and probably some of that is a derivative of the fact that the industry biases to people who are, you know, currently the average age in the U.S.
16:39of a wealth manager or advisor is somebody in their 50s. And that generally means that they've grown up under a framework of a bygone era, right? So I think that influences some of what we're seeing. But my take is that the best financial decisions and the most important decisions are made with more than math. And wealth management is just like one narrow piece, like finding alpha, growing my portfolio, that's just one input. I think about people in my life who influence the decisions I'm making, my values, the opportunities that shape the decisions. And so when people pop out of the woodwork with like zero relationship, it's very off-putting to try to like go build that relationship and help them understand contextually who I really am.
17:23What they're seeing with me is like dollar signs, like AUM, which is how advisors get paid. So I think there are some flaws in the overall model. But if I back up to kind of your core question, you know, not every founder is a certified financial planner. Let's start there. So I do think it's very true that many founders have very little financial education, particularly very young founders. Think about people who get into YC from college or they're in literally their first job as a founder. So their lived experience, they probably haven't even yet had to buy a house, run their credit for something.
17:59I mean, they're very early in their financial journey in general. And so one of the things I think wealth managers take advantage of in that situation is the lingo and the language and this almost scare tactic that gets people to feel like you don't know, but I know, so come work with me. The problem with that is that so many of these decisions start with company and corporation actually issuing stock that's QSBS eligible and maintaining your QSBS eligibility for the duration of your holding period, which, by the way, changed last year. and then understanding what you can do after you've done your first issuance of stock.
18:41Filing that QSBS in the U.S. is a major move because by doing your 83B election, you set yourself up to have some portion of your sale potentially tax-free. I have met many founders who didn't know that, missed that window. They didn't incorporate with a lawyer. Maybe they incorporated somewhere like LegalZoom and they're just too far gone to even go back and get the tax benefits, right? Then think about young founders who are going to be building for seven to 10 plus years. They started in their early 20s and what happens in their real life? They meet someone. They get married. Did they do any planning around prenup?
19:19Did they do any predetermination of if this doesn't work out and I was the sole owner of the company or a substantial shareholder? What does that mean for the wealth I'm creating? And will I have to split it and share it with someone? If my personal relationships don't work out. There are just so many questions, right? And really important ones that have to do with whether or not you might take on personal debt. Hash out your 401k plan to put more money in a business that you couldn't raise capital for. I mean, I see everything from the lens of financial planning because I'm trained to do that.
19:52And most people see what the industry wants you to see in venture capital, which is unlimited potential. do anything you can to make it work, pour your life into it. And I believe in those things with some reason and with some financial education. And, you know, when our first like$4 million seed round hit the bank, now that's not my personal money, but I remember sitting there thinking, oh my gosh, is it insured? Is this money safe? So there's financial decisions for you individually. And there are some that actually matter at the corporate level too. and most founders figure it out as they go.
20:29And if you leave people to figure it out as they go, maybe a third will split off and kind of do their homework and ask a friend and get good counseling or advice. And everyone else will probably muddle along until the day comes that they're looking at a term sheet. And now they're making an extremely high stakes decision with zero preparation and none of the upfront help and support that could have been there to get them on the journey in the right way.
20:53David Brear:Yeah, and they're pretty painful lessons to learn by getting it wrong, aren't they? So, you know, the advice you can get along the way and the advisors that can help you solve those problems on the journey is far more valued at the point where you've got to success, isn't it? The other point you made there about the sort of vagueness of language, like actually, you know, people have a tendency to use big words to try and make them feel important, but it's don't worry, I'll take care of that for you. Like, I'll deal with that. And it's, I know it's complicated. Don't worry, we'll deal with all of those things, but it's being, they're creating the difficulty themselves rather than actually it being difficult.
21:32David Brear:So it's a weird one. I mean, Kate, it's a much more emotional than rational journey, sort of building a business, I guess. And that's definitely something you've seen in, you know, the people that we've talked to as well, isn't it? Yeah. I mean, I think that kind of goes up the full spectrum of business building, right? Like, I've spoken to people that are solopreneurs, it's just them, themselves, but they are so deeply passionate about their business. And they will have responsibilities to obviously themselves, but potentially also dependents. And then you go all the way up the spectrum to companies at the scale of Aurum and things like that.
22:07So I think kind of that, I don't think you get to build a business of any size or scale without really caring about what you're building, what the precise motivations are behind that are probably unique to each person. but there is a huge amount of emotion there. And I think, again, it's, I've not had a liquidity event other than, as you were saying, like spilling some drinks or whatever. But it sounds, it feels to me, at least from the outside, like there's almost a tendency to try to minimise emotion, to try and just really present this as this is about the most rational decision and the best decision, the best financial decision.
22:41And I just love the way you spoke about it and stuff to kind of really try and create that much fuller picture about all the different considerations. But yeah, I think it's a super interesting space. And I did one of the other things that I think came out in the thread after your post, Steph, that I thought was interesting was people still saying, oh, word of mouth is so important. And actually, if you kind of get a referral, I think, and obviously, again, we see that across all of our research as well. Actually, if you can get a referral from someone that's had a similar experience to you, understands you, understands your values, your journey, your trajectory, then that is hugely valuable.
Read the full transcript
23:14But I do think it's an interesting, challenge as well because maybe it is biasing successful outcomes in this space towards people that have the right networks and the right people around them and obviously kind of one of the things that we're very passionate about here at 11FS is trying to kind of really spotlight founders businesses across the whole spectrum you know maybe people that aren't coming from necessarily such traditional founder backgrounds I wonder if some of those people are going to being particularly disadvantaged in these moments because they might not have the friend next to them that's done it before.
23:46They might be forging the path for the first time. Steph, you're pointing it better than me. You're absolutely right, Kate. I mean, I think like all things in financial service, the kind of key principle is if you start with access, you have access. And if you don't start with access, you're in a more challenged position to educate yourself and kind of gain traction and control. A good founder friend of mine, and she's a first-generation U.S. immigrant. She's building a business in the CPG category. And we were chatting the other day and she said, I honestly don't know, Steph. Like, I've been so heads down making this work, figuring out my product and my distribution.
24:25If I had to sell the company tomorrow, I don't know what I would make. I actually don't know how much I own of this company. And she's done multiple rounds of safe notes, so then they convert. And she's really in the dark about a lot of the decisions that affect her and her outcome. And there is no one tapping her on the shoulder pre an exit saying, let me help you figure this out. And I think that's such a miss because in a lot of cases for this to all be interesting, you don't need to have a billion dollar exit. You actually don't need generational wealth. Some people might walk away either as founders or even as operators in a company with much smaller dollars that they're receiving.
25:07but those are life-changing dollars. Remember, the average American does not have$400 in their bank account to pay for an emergency, okay? So when we get into the venture capital ecosystem and the noise and cognitive dissonance of generational wealth starts to set in, I think we lose sight of the fact that many founders have, one, potentially put all of their life savings, if they had any, into their business. Two, are undereducated. And as a result of that, they lack confidence in being able to navigate the decisions. And so much of that confidence is a derivative not of ego. It's a derivative of knowing if A, if B, what are their results, right?
25:45Because if you go to sell a company and you make a decision about taking cash versus stock, there are so many different permutations of making this valuable to you in different ways, tax-friendly. And I do really feel that the system does not only not support founders and people who operate in tech, it doesn't support people who don't start with wealth and or who don't kind of grow up in the system where they inherit their parents' financial advisor, or they have a friend who can make that referral, which is exactly why I think there's white space to build something that's never really been done the right way before.
26:22As I'm conceiving of pretty smart money, I'm not ready to say all the things it is and will do. I have a very unique take on how you would help someone find an advisor who gets them, right, really understands who they are and what they want, and can work with them in a way that helps them plan the entire trajectory, not just this single moment in time.
26:43David Brear:Sounds fantastic. We'll definitely talk about that a little bit more in the second half of the show. We're going to come back to you. We're going to be exploring what the next generation of financial advice could actually look like, whether AI, fintech, and new business models can actually build that trust that we've been talking about. So, be back with you really shortly.
27:06David Brear:Welcome back, everybody. In the first half of the show, we explored why traditional wealth management often arrives a little bit too late after the big financial decisions have actually already been made. So if that is the problem, then what really should replace it? Steph, I mean, you said going through this process has changed how you think about that exit. And obviously, in the first half of the show, we talked about the need to really get a very long run up in that space. But, you know, I guess we're talking about quite a different approach to financial management. I mean, it's not about wealth management.
27:40David Brear:It's more about the sort of construction of wealth in its first principle, I guess. Yeah, exactly. I mean, I think wealth management like diminishes it, right? Because it actually narrows it to thinking only about your portfolio. And that is important as you have the ability to invest and grow your assets, whether through a liquidity event or through some other avenue. Wealth is one part of the picture. But income streams and various income streams, not just a salary, but other ways to generate income are as meaningful as potentially building up your wealth portfolio. So I think it just, the word itself like misses the broader opportunity of thinking about a comprehensive set of inputs and outputs that help you pay for the life you want now and build for the life you're going to have in the future, which may or may not include having this traditional nine to five full-time career path.
28:29And so when I think about like today's industry in the U.S., Part of the reason I think that the cold outreach and this sort of like ick factor exists is because the model essentially says you don't get paid on anything other than assets or products. So if you can get assets under management, you will make money. And so, you know, the industry has trained advisors to go seek that out. And hey, if you can give some advice on the perimeter, it's not bad. But the way we're licensed in the industry, the way we're compensated, it all drives back to assets under management, which then silences the conversation.
29:08And I've never had a conversation with a traditional wealth advisor that encourages me to think about how I might make different career choices. Should I take this compensation package that biases to a big bonus that I don't have total control over? Or should I take one that biases to higher cash? Should I look at a job that has better benefits for certain things versus cash compensation? I mean, there are myriad choices to make. And so I think about the framework a little bit differently. Because again, kind of confidence is the emotional outcome that I think is the win. Money will be part of that, but the emotional outcome is part of this.
29:48And so for me, there's four things. If you were making a high stakes financial decision and we were not calling it wealth management, I'd think about your math, right? Like understand the numbers, the trade-offs, the timing, and the possible outcomes. Possible outcomes being an important one because so often you don't know what a downside scenario might be versus an upside. You really only think about the big ones. Number two would be your tribe. Consider the people whose lives, perspective, and support matter. I'm married to someone who is infinitely supportive of my crazy dreams to build things.
30:20And still, I don't make a decision without saying, like, how will this affect our household? Is that the right decision for us? I recently walked away from an opportunity in one of the hottest startups in New York and really almost in the world right now to take a very senior role for a, call it, nine-digit compensation figure. And there were a lot of red flags. And my husband was like, but we don't need$100 million. And why would you want that job? And I had to really dig deep on, you know, my tribe. And I think there's a third pillar, which is what I call your compass. So aligning the decisions with your values, your risk tolerance at what matters most in your household, your family.
31:01And then last is your growth. Skills, relationships, opportunities that compound over time. The strongest decisions have all four of these together. And not once you can be talking about your portfolio. It's in there, but it has nothing to do with the kind of framework for making the big decisions. And to me, that's what's missing.
31:20David Brear:Definitely. I mean, as you say, that's a decision-making criteria rather than a financial instrument in that sense. I mean, it's bizarre how often, and Kate, I mean, there's at least 700 episodes of this podcast where we've talked about this. So strap yourself in, everybody, listening to this. But for me, as you say, the irony that financial services is called financial services when the service is completely missing, right? All of the benefits, as you say, are driven by the selling of financial instruments or products rather than actually the thing that you need. That confidence and those four factors that model creates, if you get those things right, is a wealth or whatever size of it or lack of it or whatever becomes a background factor to life, not the foreground factor, doesn't it?
32:12David Brear:And that's a strange thing that people miss from these things, isn't it? Again, it's, but you can't, there's nothing that hacks you quickly to fulfilling those four corners. All of them require actually thinking about it and ongoing trust from it. And, you know, I think with the wealth industry as well, I mean, the difficulty with fintech more broadly has been that it is approached retail banking, commercial banking, payment structures as a self-service thing that you can just move all of the decision-making criteria onto the customer. But those things that you were just describing, Steph, require somebody to A, point them out to you, and then somebody to help you, guide you through those processes.
32:55David Brear:Because it's pretty hard to do self-reflection on your own sometimes, isn't it? You have a million blind spots, and you have your own emotions, and you have a bunch of input. So when you're able to work with somebody who has your best intentions and outcomes in mind. It's a fundamentally different relationship. It's kind of like personal trainer, right? Of course I could, Kate, you could get on that Peloton and there are great content classes on it and strength training is one of them, but I'm never going to work as hard or even do the poses and postures, right? If I'm not potentially with somebody who's coaching me up, right?
33:29So I think a lot about that, like it's a really simple analogy, but health and wealth actually do fit really nicely together. and you had your own blind spots. No one ever does it as well as they could if they had a professional in their life. And I think that's kind of the thing I always come back to. And Kate, I'm not saying you don't ride the Peloton. I'm sure you do. I ride mine. But I do ride the Peloton, but I do also use a coach to make me do the right things, right? So yeah, I completely agree with that analogy. I mean, one thing that I thought was, I was particularly interested as I was listening to kind of those four pillars you were describing, I think was the tribe component and I think we're often quite critical about social media influences, people getting advice from social media but I do think that kind of tribe component is maybe part of why social media, financial content on social media is so compelling because if I think about the things that come up on my feed, you know, it's all coming from mostly women that look a bit like me and they speak about similar life stages to me, similar career choices to me, because the algorithm has kind of worked out that, you know, I'm going to be much more likely to interact with content that seems like it's from my tribe or somebody that I would recognize their life experience in my own.
34:48And so I think, yeah, a part of, yeah, that's just such a really interesting pillar to think about because I think at the moment it's not being served and that's probably why we're seeing so much, so many eyeballs on social media content because it's filling that gap and people aren't getting that support elsewhere. Well, I think, Kate, you point out something so different in today's version of social media. I often joke with Alexa Montobo, who was the founder of LearnVest, we would have never sold LearnVest if today's version of social media had existed. And I say that because in the decade plus since we sold LearnVest to North Western Mutual and in the 20 years plus that I've been a financial planner, I got my CFP in 2006, like really three things have gotten better.
35:32Number one, direct indexing is cheaper and easier. Number two, you can buy fractional shares, and that's great. And that used to be hard, and now it's easy. And number three is social media. It's the algorithms are really dialed to a place where you can find the voices who have the knowledge, potentially the trust. And Kate, I don't think it's necessarily a bad thing to consider some of that content a part of your tribe as an extension of the tribe, perhaps. But to me, that's actually one of the most meaningful and influential differences. It used to be like your uncle, your brother, somebody in the family.
36:08And as a financial planner, I would always hear from people how they got their tips and advice. You know, Kramer, there was like a few faces out there, but not many. And not many that looked like you. And I do think that that is one of the big transformations that will continue to influence. I mean, TikTok not only saved books, thanks to BookTok, but they are definitely playing a huge role through FinTalk in how people access information, not only about the concepts, but sometimes about products that are the right fit. And I'm not averse to products, by the way. We said financial services buy assisted products.
36:43There's a time and a place for some of them. It's just a matter of like, knowing that they're really a great fit for you and knowing how and when to think about those products entering the planning that you're doing. Yeah, definitely.
36:55David Brear:The sort of finding a community that's been through similar things who can guide you through those is really important, isn't it, in that sense. I guess the sad part really is that we're still not getting that service though from traditional players, are we? We're living in a world where, as you say, video content can be so heavily personalized to each individual, but actually still it's a random dude on LinkedIn reaching out. I know I've said on the podcast before but my sadly when my dad passed away and my mom inherited uh everything from his side then first thing she did was move all of the money away from the bank that she was with because they basically alienated her for 30 years you know like so so the the experience is not uh has not moved much further forward i would say with a lot of the traditional players it's it's very much the how nice is the pen and how nice is your suit and uh you know how thick is the pdf you're sending to everybody to make them feel the value rather than actually generating it, isn't it?
37:55David Brear:So, but I mean, Kate, that feels like a gap. It feels like technology can kind of address these problems now. So why is that not happening? Well, I mean, first of all, I do love a good pen. So like in some ways I feel like it, yeah, I know, I know what my actual like informed brain should be thinking about, but part of my brain is going, I really want a pen. But no, let's be serious, I mean I think part of the challenge is that financial services is just such a heavily regulated space like you know we can't we know what the customer outcomes are that we want but these are regulated products that come with costs and so I think we're still just not seen certainly in the UK I'm not as up to speed with maybe the US pitch I'm sure Seth will have that lens but like I just don't think people have got their heads around how they make it commercially viable to offer financial advice to more people, which means, as you said, we're saying people are waiting for that moment when the assets under management are there just to pick up and run with.
38:57So yeah, I just don't think we've seen people think innovatively enough about how they make money from customers. And that sounds like it should be a negative thing. It sounds like it should be, I'm meant to be a sort of customer researcher. Why am I talking about making money from customers? But good customer services, good customer outcomes aren't sustainable unless these businesses are able to cover their costs and make profit and scale efficiently. So I think we have to really come back to trying to find ways to make providing advice more cost effective. Obviously, AI potentially is going to play a huge part in that.
39:36And we're still just trying to understand how that's going to play out. Certainly, we've seen initial movements from the FCA in the UK talking about kind of the interrelation between AI and advice. But yeah, we haven't really seen that ripple down into actual customer facing propositions yet.
39:51David Brear:Yeah, I guess on the point of making money, I mean, definitely we've seen weird things happening in the market lately, haven't we? We've seen, you know, Coots in the UK, Steph, you know, used to be the Queen's Bank. So it's very fancy. They've raised their limit, the minimum, sorry, from a million pounds to three million pounds in an attempt to make sure that actually there's money being made from those accounts. We're seeing gigantic wealth providers offboarding customers in the range of 500 ,000 to 750 ,000 because they can't make them profitable. And actually, that's a weird place to be, isn't it?
40:26David Brear:If you can't make somebody with 750 ,000 pounds under management with you profitable, that's not a good sign that actually your back office is cost efficient, that you're not layering people over bad processes to solve. And I think that really that's possibly the opportunity. But I guess as Kate says, the advancements in technology and particularly with AI, that feels like quite a big opportunity to turn that around. I think AI is going to be incredibly influential in the back and middle office. I know we're in the U.S. seeing, you know, some early things with ChatGPT and Plaid as partnerships to basically say, link all your accounts and we'll give you financial advice.
41:07And I really don't think that is the answer. If I come back to that framework, right, it's like that misses all the key things that we were just talking about. And it also misses something where I feel like human advice has an irreplaceable component that I call emotional optimization. And there's a financially optimized answer to every mathematical input, but there's also the emotional optimization. I'll give you an example. This is what's about founders, and this is just more general sort of, you know, financial planning. When people have debt, which is in America, unfortunately, very common, there are high interest rate debts and there are low interest rate debts.
41:45And generally speaking, we're going to want to try to help you pay off your highest interest rate debt first because it's the one that like compounds like rabbits, right? It just keeps getting bigger because the rate is so high and the compounding is so fast. And so if you're talking to somebody and they have debt to pay off and they say, listen, I know that I should pay off this high interest rate card first, but the student loan debt that I've had for a decade is embarrassing, makes me feel bad every time I look at the balance. And if I'm picking the$100 to go somewhere, I'd really like it to go there.
42:17That is as good of a decision as the high interest rate debt because it's progress, right? And if you were to just have a chat GPT answer, the math would always bias to doing the high interest rate problem first. And for many people, progress is an incredible drug. Okay. I'll go back to the Peloton, right? Why does fitness start with like 20-minute classes and 10-minute things? It's so that you can go on the journey to eventually run a mile or complete something material. And I think about wealth and financial planning in the same way. If you have$5 to put towards something, $5 is better than zero.
42:56And so just start. And I think sometimes that is missed. And this is where there could be plenty more education going all the way back to school, right? In our education system in the U.S., you learn nothing, nothing about what it's going to take to make financial decisions. And then you're thrown into the world and you have all of this stuff and it's noisy. And then we get into the problem of financial products being out there and not having a real understanding of what they do. So while I'm very pro-AI, and I would say in the U.S. in the wealth management space, we're seeing interesting interns like Humanity Labs coming in to really optimize with agents, that middle and back office.
43:36There was a ton happening with Hazel by Altruist for CRM management and financial planning, just optimized with data that's getting collected through calls and emails. Those are going to be amazing game changers, I think, in the cost structure. we still need that human. I think we're going to see like a concierge level service become very, very, very valuable. I think about it a little bit like when I'm trying to navigate a canceled flight and I'm stuck in an airport. All you find people doing on the phone is saying operator, operator, like trying to bypass, right, the automation. Humans are going to be a premium.
44:16And in the U.S. market, we don't have enough people who enter the financial advice category as a career, there are only about 100 ,000 people considered advisors or financial planners. And some of our biggest wealth management shops and broker-dealers, their number one concern is staff, right? So that to me says premium for human interaction. Portfolio optimization, stock picking, I mean, all of that stuff is just going to continue to get more and more and more AI optimized and honestly, like, less differentiated by firm. Those are commodities. The non-commodity is the relationship and the person who gets you and gets that list of things that your tribe, your values, your math, they all come together in a central way.
45:00So that for me is something I just hold really tight as I think about what this future looks like.
45:06David Brear:Yeah, I think that's super right. It's going to be amazing to see how far through that journey the technology can go. The trust, the confidence that you talked about earlier on, the proactiveness that can come with that, not just waiting until somebody's got a problem or waiting until they come to you, but actually proactively dealing with problems for people. it changes the context of financial services again, doesn't it? Which is, you know, it's quite an amazing thing to think about, isn't it? If your life was something that financial services was being done for you, how different would that feel than just the thing at the back of your head that you know you need to deal with that paperwork or this thinking or saving for college or whatever, You know, it's a different feeling for life, isn't it?
45:59David Brear:Which makes it sound so fluffy, but that's what it's all about, isn't it? As you said earlier on, the confidence of, you know, being able to sleep easy every night because you know these things are taken care of is something that I personally would pay for, for sure. But what do you think, Kate? Like the technology is disrupted. Pretty much every financial services slither, you know, all around the world. But still, we're seeing a lot of FTPs with PDFs being sent down them. Like, you know, the wealth space definitely has a long way to go. Yeah, absolutely. I think Steph's completely right to call out that I do think the ideal endgame will be technology plus people.
46:43Like, I think that is the ideal outcome. I suppose I worry that people are going to get so excited about AI that similar to what we saw with the arrival of digital banking, generally people's first instinct will be to just try and move everything into kind of, can we funnel everything through AI in as regulated way as possible to kind of strip out as many humans as possible and it'll probably take that system to fall short or to break or to not achieve the outcomes that some of these companies are hoping for for them to realise that they have to put some of the people back in. I guess maybe that's my pessimistic interpretation, but maybe with the likes of founders like Steph pushing on to their next ventures, maybe we'll get there a bit sooner, but fingers crossed.
47:23David Brear:So what do we expect then? Five years from now, obviously Steph by then, pretty smart money is going to be ridiculously successful as well. Yes. But what do we reckon in five years time? What is this space going to look like? Steph, maybe starting with you. Yeah, well, as we said, I think the human's going to be at the center of it. And so I'm excited to continue to see humans in the financial advice arena. But more importantly, I think that execution is going to be the really critical next layer of investment that's really never been completed. So I'll give you an example. Right now, we have all this talk about agent at commerce.
48:00And I'm going to have agents who are going to go buy my trips and plan everything for me. And we are starting to see real inroads in payments for that. I think if you apply that same execution lens, when you're doing financial planning, there are lots of things that get said that are the next important step. And they require a login and a password and permission. And so the financial planner is stuck just emailing you, texting you, like reminding you to do it. And if you're me, you're like, I have great intentions. I'm going to get that rollover from my husband's old 401k taken care of. but it requires a phone call and it requires a form and I'm busy.
48:40So I think execution is going to be hugely important and probably a fee surface that's never been touched before. When I recently updated my estate plan, you know, estate plans, like all things, are great pieces of paper. They're only good if you actually go to retitle your property, your assets. Guess what? The house I'm sitting in has not been retitled in the name of the trust. But an agent could easily optimize every state, every municipality, and make those changes. So when I think five years out on the horizon, I think the human's still the central point. I think we're talking deep emotional optimization so that this works the way I just described.
49:20I think it will. And then like the minutiae of making those things actually come to life. This is where the cost consideration used to be a problem and I think won't be as agents for execution really do enter the picture in a meaningful way. And I hope it doesn't take five years, by the way. I really hope it doesn't.
49:38David Brear:Well, it sounds like you're going to be building it. So it sounds like it's up to you how long it takes. Kate, what do you think? Five years from now, what are we looking at? What does the industry look like looking back from then? Yeah, I mean, I don't think I can necessarily top what Steph described. I definitely think it will be fundamentally different because of the arrival of AI. I mean, I suppose the other thing that I'm seeing from the conversations we're having with eBanks and Cummins FinTechs, I think more and more people are kind of waking up to the fact that they need to start thinking less about individuals and more about family units.
50:11I think people are kind of starting to realize that their customer base is just aging and the bottom of that funnel is not topping up in the way they assumed it would necessarily or not looking quite the same. so I do think in five years time we'll have platforms services support that yes serves individuals but also has to try and think about kind of broader structures families household units in different ways to try and fit with the way in which people's lives actually work and so yeah a lot of AI hopefully some more family structured money and hopefully better outcomes
50:45David Brear:definitely I think that that would be the wild add I think it's just better outcomes for everybody Ultimately, that's what every regulator around the entirety of the world wants is good, consistent outcomes from people. And the advancements in technology definitely can lead to that, you know, evidencing why every piece of information led to a specific piece of advice. That's a dream from a regulator's perspective, not sort of dusty old bits of paper, but much better services for people, which is a you know an interesting thing that that would be a step forward that suddenly we you know five years from now we start getting good outcomes weird right um all right well before we wrap up one sentence right well maybe even let's go even shorter like kate the future of financial advice is what better i'd like it like it steph about the whole person i like it contextual to everybody in that i feel like we've done a lot i don't even have one that can top either of you to or even come close, so I'm not even going to try.
51:44David Brear:So on that note, we better wrap up this discussion. And Steph, when you can come back and tell us more about your new company and the sort of run you're going to plow with that one, we would love to hear it. But for anybody trying to get in touch with you now, and I presume not stuffy old, dusty old wealth managers into your DMs, but Steph, where can people get in touch? You can find me on LinkedIn. You can also follow Pretty Smart Money. And for those that want to watch my very embarrassing social media journey, I am on TikTok and Instagram as SKPCFP. So come have a watch. It's interesting being in your mid-40s, getting in social media.
52:21So come have a look.
52:22David Brear:Sounds like fun. Sounds like a lot of fun. Kate, where can people find you more? LinkedIn, probably the best place. I mean, I have Instagram, but it's mostly just pictures of my children. So I don't think that's going to be of interest to people. So yeah, LinkedIn's probably the best bet. I feel like they might enjoy that. You know, you never know. Get involved with, you know, Kate's journey through motherhood as well is always an interesting one. As for me, just drop me an email, david at 11fs.com. I hope you've enjoyed this podcast. Thank you so much for listening. If you do like what you've heard, follow our podcast and don't forget to leave us a review.
52:55David Brear:It helps us make the show better and helps other people find it as well. As always, if you want to join the conversation, you've just been shouting at your earphones of something that one of us said and you want to correct us or thank us or anything in that sense. Find us on any platform from a social media perspective. Just search for 11FS or FinTech Insider. Or if you really want to, email us on podcasts at 11FS.com. Thank you very much for listening, everybody. Goodbye.
53:25David Brear:I don't think I can be your friend, Isabella said. Rebecca's stomach flipped. This is the love story of real hinge couple Isabella and Rebecca, written and read by me, Temi Denton-Hurst. Listen to the free audiobook now.
53:42Hello.
53:43David Brear:Look what TJ Maxx dragged in. The Devil Wears Prada 2 is now streaming on Disney Plus and Hulu. We are digital. We are downloadable. We are streamable. The fashion event of the year is certified fresh. Pull yourself together. We have work to do. Critics say it's smart and witty and the perfect sequel. That's all. Get runway ready for The Devil Wears Prada 2 on Disney Plus and Hulu. Rated PG-13. Hi, Ryan Reynolds here for Mint Mobile. Are you looking for a beach read this summer? May I suggest your big wireless bill? It's got suspense, mystery, a slightly flat emotional arc, and a shocking twist where you realize you've been overpaying the entire time.
54:24David Brear:Fortunately, though, Mint's story is better. Every plan,$15 a month, even unlimited. That's it. Happy ending. Zero tears. Give it a try at mintmobile.com slash switch. Upfront payment of$45 for three months,$90 for six months, or$180 for 12-month plan required. $15 per month equivalent. Taxes and fees extra. Initial plan term only. Greater than 50 gigabytes may slow when network is busy. See terms.
From the publisher
About this episode:
For many founders, selling a company is seen as the finish line. But some of the biggest financial decisions around an exit happen long before the deal is done - so why does wealth management so often arrive too late?
Host David Brear is joined by Stephany Kirkpatrick, founder of Pretty Smart Money and Orum, and Kate Moody, Customer Strategy Director at 11:FS, to explore why traditional wealth management struggles to build trust with founders, what major life events reveal about the industry's product-first approach, and how better planning, technology and AI could reshape the future of financial advice.
This week's guests:
Stephany Kirkpatrick - Founder Pretty Smart Money
Kate Moody - Customer Strategy Director at 11:FS
Links to check out:
Join our WhatsApp community, where you can get the inside track on all all things 11:FS, as well as having your say on the things we should be paying attention to.
https://chat.whatsapp.com/KpA4gFbbWDlLFm7kx39raf
About Fintech Insider:
Fintech Insider by 11:FS is a bi-weekly podcast that covers everything from finance and banking to technology and the latest trends in financial services.
Our expert hosts, with hands-on industry experience, are joined by key decision-makers, VCs, and top reporters from across the financial landscape, including guests from companies like Stripe, Revolut, Plaid, PayPal, and Monzo. Together, they break down the biggest news and innovations shaping the space.
Our weekly news show drops every Monday, covering major stories like mergers, new product launches, regulatory shifts, and emerging tech trends. On Thursdays, our Insights show goes deeper into the hottest topics driving the future of finance, including AI in banking, decentralised finance, and the evolving landscape of embedded finance.
Whether you're already in the fintech game or just starting to explore, this is the #1 podcast for you.
If you enjoyed this episode, don’t forget to subscribe and leave a review!
Got a question for us? Email podcasts@11fs.com!
Learn more about your ad choices. Visit megaphone.fm/adchoices




