Search Interviews:

[EO San Francisco] Building a Resilient Advisory Practice in Uncertain Times With Will Richardson

[EO San Francisco] Building a Resilient Advisory Practice in Uncertain Times With Will Richardson

Will RichardsonWill Richardson is a Financial Advisor with Pacific Prosperity Partners under the Northwestern Mutual umbrella. He helps individuals and families navigate uncertainty through thoughtful, long-term financial planning. Having started his career during the 2008 financial crisis, Will brings firsthand experience guiding clients through market volatility and major life transitions. He is also the host of the 10X Podcast, where he shares insights on communication, leadership, and building resilient advisory practices.

Spotify
Apple
Amazon Music
Tune In
Stitcher
iHeart Radio
Deezer

Here’s a glimpse of what you’ll learn:

[01:54] Will Richardson shares how a childhood cassette tape podcast sparked his entrepreneurial spirit
[04:48] Why Will’s fear of sales didn’t stop him from succeeding
[08:14] Proven strategies to grow a network from scratch
[12:23] Tips on calming financial volatility anxiety amid relentless negative news
[15:51] Northwestern Mutual’s unique advisor business structure explained
[17:43] The impact of podcasting on business growth and client relationships

In this episode…

Uncertainty has a way of exposing the cracks in some of the most successful businesses. When markets swing, headlines fuel anxiety, and clients feel uneasy, what can help a financial advisory practice remain stable and continue to grow?

For Will Richardson, a veteran financial advisor, the answer starts with having a plan built for turbulence, not perfection. He explains that market drops, political shifts, and ominous headlines are not exceptions but regular features of the financial landscape, and resilient practices prepare clients for that reality upfront. When expectations are set correctly, uncertainty becomes something to navigate calmly rather than something that derails long-term decisions.

In this episode of the Rising Entrepreneurs Podcast, John Corcoran is joined by Will Richardson, Financial Advisor with Northwestern Mutual’s Pacific Prosperity Partners, to discuss building a resilient financial advisory practice in uncertain times. They explore how advisors can help clients stay focused during market volatility, why long-term planning matters more than decisions based on the latest headlines, and lessons learned from starting a career during major economic downturns.

Resources mentioned in this episode:

Quotable Moments

  • “I just remember having fun with it and just having real and fake conversations on cassette tapes back then.”
  • “We have to show that we understand the situation and why they’re concerned about what’s going on.”
  • “What we’re seeing is a lot of private equity money come in to start to acquire some of these smaller operations.”
  • “There’s always going to be uncertainty.”
  • “Their plan was built to withstand whatever might happen.”

Action Steps

  1. Build financial plans that assume volatility: Preparing clients for downturns upfront reduces panic and supports better long-term decision-making.
  2. Focus client conversations on understanding, not headlines: Acknowledging concerns while reinforcing the plan helps clients stay disciplined during uncertainty.
  3. Leverage existing relationships for growth: Warm introductions from trusted contacts create stronger connections than cold outreach alone.
  4. Develop systems that support resilience, not heroics: Consistent processes and team coverage ensure stability when unexpected events occur.
  5. Use content and conversations to educate at scale: Sharing insights through podcasts or discussions builds trust and reinforces expertise over time.

Sponsor for this episode…

At Rise25 we help B2B businesses give to and connect to your ‘Dream 200’ relationships and partnerships.

We help you cultivate amazing relationships in 2 ways.

#1 Podcasting

#2 Strategic Gifting

#1 Our Predictable Podcast ROI Program

At Rise25, we’re committed to helping you connect with your Dream 200 referral partners, clients, and strategic partners through our done-for-you podcast solution.

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

What do you need to start a podcast?

When you use our proven system, all you need is an idea and a voice. We handle the strategy, production, and distribution – you just need to show up and talk.

The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

We make distribution easy.

We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Amazon Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90x, Atari, Einstein Bagels, Mattel, Rx Bars, YPO, EO, Lending Tree, FreshBooks, and many more.

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win?

Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

#2 Our Comprehensive Corporate Gifting Program

Elevate business relationships with customers, partners, staff, and prospects through gifting.

At Rise25, thoughtful and consistent gifting is a key component of staying top of mind and helps build lasting business relationships. Our corporate gift program is designed to simplify your process by delivering a full-service corporate gifting program — from sourcing and hand selecting the best gifts to expert packaging, custom branding, reliable shipping, and personalized messaging on your branded stationary.

Our done-for-you corporate gifting service ensures that your referral partners, prospects, and clients receive personalized touchpoints that enhance your business gifting efforts and provide a refined executive gifting experience. Whether you’re looking to impress key stakeholders or boost client loyalty, our comprehensive approach makes it easy and affordable.

Discover how Rise25’s personalized corporate gifting program can help you create lasting impressions. Get started today and experience the difference a strategic gifting approach can make.

Email us through our contact form.

You can learn more and watch a video on how it works here: https://rise25.com/giftprogram/

Contact us now at support@rise25.com or message us here https://rise25.com/contact/

Episode Transcript:

Intro: 00:02

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

John Corcoran: 00:12

All right, John Corcoran, here I am, the co-host of this show. And you know, every week we have smart CEOs, founders, entrepreneurs from all kinds of companies here on this show. And before we get into this, my company is Rise25. I’m the Co-founder of Rise25, where we help B2B businesses to get clients referrals and strategic partnerships through done for you podcasts and content marketing. And I’m also a board member of EO San Francisco.

And this episode is brought to you by EO San Francisco, which is the San Francisco chapter of Entrepreneurs’ Organization, which is a global peer to peer network of more than 20,000 influential business owners across 200 chapters, 60 plus countries. And if you are the founder, co-founder or controlling shareholder of a company that generates over $1 million a year in revenues, and you want to connect with other like minded, successful entrepreneurs. EO is for you. And so you can learn more by going to. San Francisco.

I’m excited for today’s guest. His name is Will Richardson. He’s a veteran financial advisor and Managing Director for Richardson Financial Wealth Management and Insurance Services. It is an advisory team within the Northwestern Mutual umbrella. We’ll say we’ll get into that in a second.

He has over two days of experience in the financial services industry, and he’s also the host of the 10X Podcast, where he shares tools and insights for clients and fellow professionals in the industry. Will, excited to have you here today. And you’re a newer member of our chapter. And we were talking beforehand about the young Will Richardson, who had a quasi podcast back in the day. In fifth grade, you had a podcast on cassette tapes.

I want to hear about this podcast. And cassette tapes was like.

Will Richardson: 01:54

Well, first of all, thanks for having me, John. I’m really excited to be here with you. Yeah, I was thinking about that. So when I was in fifth grade, I would, I suppose would be the equivalent of having a podcast or a YouTube channel now. Yeah, my 12 year old has a YouTube channel, and back then I would just talk to people and record it, and sometimes I couldn’t find anybody to talk to, so I would I would impersonate multiple people and have them on and it was fun.

I just remember having fun with it and and just having real and fake conversations on cassette tapes back then.

John Corcoran: 02:24

That’s great. And you grew up in Mississippi. Quite a different world you are in now here in San Francisco. What was your upbringing like? Was it a family life like as a kid?

Will Richardson: 02:36

Well, yeah. So I lived there through college. I graduated from Ole Miss and I haven’t lived there since. I would say that growing up there was, was was good. I mean, I, I wasn’t into sports or anything like that as, as a kid.

What I do remember doing is going to Ole Miss football games with my dad. Like there were a couple of years where we went to every single game, and that meant we would drive to Lexington, Kentucky or Gainesville, Florida, wherever the games were, we went. So I didn’t play sports, but I became a big fan of Ole Miss sports when I was growing up there. And so then I wound up going to school there when it was time.

John Corcoran: 03:13

I was trying to explain this to my kids. This weekend. I’ve got a couple of kids that are into watching football, and we were watching college football. I think it was a Penn State game and it was packed. Tons of people, just so much energy there.

And and actually, my 11 year old had just been to see a Cal football game a couple of weeks ago, and he was like, dad, there’s there’s a lot more people in that stadium than there was at the Cal football game. And I was trying to explain to him that, you know, there there are parts of the country where, you know, that type of thing is a huge event in the city, and everyone talks about it, everyone goes to it. And it’s just kind of hard to convey the cultural impact that, you know, college football can have on a town. Is that a little bit of what you experienced?

Will Richardson: 03:54

Oh, yeah. Growing up in Mississippi, SEC football, Whoever your team happens to be, it’s a big deal. And now, yeah, these college stadiums are bigger. A big one is bigger than an NFL stadium. Yeah.

Now they’ve they’ve got all these these ways they’re paying players. And so it’s it’s changed a lot. It was always a big deal. But I think it’s become an even bigger deal over the last handful of years.

John Corcoran: 04:17

Yeah. So you before you get into advising people on financial management and wealth management and stuff like that, you had kind of a typical straight path. You went straight into compliance, right? I’m just kind of joking here. But compliance, that’s not the usual route you like.

You were like helping, I guess the advisors with compliance issues. That’s not usually the route into then, you know, doing sales and client management and stuff like that.

Will Richardson: 04:48

Well, have you ever known somebody that’ll say to you like, hey, John, I’m just not good at sales. I could never do sales. Like I couldn’t sell anything. Like, people say that to me sometimes, and that’s exactly the way I was. I wanted anything but a sales role.

And I think part of that is because I came out of college, I had two sales jobs. One, I was selling golf clubs right out of school. I don’t play golf. I never did, so that was challenging to sell golf clubs over the phone. Occasionally people bought one, but I didn’t really.

I wasn’t crushing it. And then at Morgan Stanley, I just didn’t have the maturity. So I got my licenses there and sold literally nothing to no one. Like it just wasn’t.

John Corcoran: 05:27

Didn’t you also sell Cutco knives to in college?

Will Richardson: 05:30

Oh, yes. No, that was a little bit better. That was my first kind of sales entrepreneurial role. So I did that for a little while when I was at Ole Miss. And and that went better than the golf clubs or the Morgan Stanley part.

And so the compliance thing was, was mainly because.

John Corcoran: 05:46

I want to ask you about that, though. How did you end up selling Cutco knives? Everyone who I’ve met who did that in college, they seemed like people that are drawn to sales usually. So how did you find yourself in that? For someone who, you know, you admitted, you said that you weren’t drawn to sales.

Will Richardson: 06:05

Well, that was part of how I figured it out. You know, my longest job when I was in high school. I worked at Wendy’s in high school and college for about three and a half years. So I learned how to work really hard in that you didn’t make a ton of money. And one day there was a a flyer that Cutco had put on everybody’s windshield outside of, you know, classes.

And so I called them and I went and had a conversation with them and, and figured I would I would give it a shot. So that was I did that for probably about six months or so and, and I was I was okay at it. And I just remember, you know, you could you could earn money. I remember doing demonstrations of cutting a penny in half with a pair of scissors. There was a thing where you would you would cut a rope in half, like you had this whole kit with you of things to demonstrate.

And by the way, this was in the late 90s, and my family still has those knives and they still they’re very high quality. If you have a chance a to buy them, do it. Or B to recruit someone who sold them. I would do both of those things.

John Corcoran: 07:04

Yes, I have a cutco knife at my house and it is amazing. Yeah, they do an incredible job. All right. So that’s your background. So you end up in compliance and you end up in Florida doing compliance.

And then eventually you make it to the Bay area. And you how do you go from compliance to then, you know, in more of a sales role?

Will Richardson: 07:24

Well, there are a couple of things. One, my ex-wife, we’re no longer married. We have two great kids together. We were dating back then and she encouraged me. She thought she saw that I had a potential to do more than I thought I did back at that time.

And also the veteran advisors did. So I got to know the benefit of being the compliance person is you sit down with everybody in the organization and, you know, a lot of it was making sure people are up to date with whatever the rules are, whatever we’re supposed to do or disclose and all that stuff. And multiple advisors said to me, like, we think you could do what we do. And eventually I decided to give it a shot.

John Corcoran: 08:02

And where do you start when that’s when you’re new to that role. Like you start like knocking on doors. Do you start networking? Where do you where do you get your initial clients from?

Will Richardson: 08:14

Anything you can think of? You know, the Morgan Stanley training was here’s the yellow pages or the white pages. Just cold call people. The Northwestern Mutual training, which worked better for me. It’s really about getting connected to people by people that you already know.

So you start out, you make a list of essentially everybody that knows you and likes you and that you could sit down with. And mostly those people didn’t become clients, at least not for me, and certainly not right away. But I would look for ways to get them to introduce me to people that they knew. And so that was more or less how it started. And then eventually I figured out that I liked working with attorneys.

And this is back in 2008. So everything was in person. So what I used to do is I would, I would let’s say I schedule a meeting with you and, and you’re at a firm in San Francisco. I would then aim to schedule 3 or 4 other meetings with people at that same firm. And that was even more important if I was driving, because, you know, most of these firms would have a San Francisco office and a Silicon Valley office.

And I learned the hard way about having one meeting in Palo Alto, because I got stood up and that, like, blew up my morning. So from then on, a I confirmed the meeting, but B, if I was going down there, I would have 2 or 3 meetings at a time to make it worth, you know, the effort of driving down there.

John Corcoran: 09:30

I’ve seen people do this where like an office I’m working in, someone knocks on the door and they’re like, yeah, hi. I’m from, you know, Xerox copier machines or something. And I’ve got a, you know, appointment down the hall from you, and I thought I’d just stop by. Is that the sort of tactic that you would use, or how would you get multiple meetings in the same place?

Will Richardson: 09:53

I wasn’t brave enough to do that. That. So it was. It was calling. I would I would make phone calls ahead of time.

So it would be, you know, I was usually looking to schedule things for next week. So if I knew I was going to be down there next Tuesday, then I’m calling you today to see if you happen to be in the office on Tuesday, because I’m meeting with, you know, whoever else in the office there.

John Corcoran: 10:13

Yeah, of course, 2008 was a bit of a calamitous time for the investment landscape, famously. Right. We had the Great Recession or whatever we call it, was that looking back on it now, is that a good time for you to make this career shift?

Will Richardson: 10:30

You know what the best part about it, John, was that no one else would hire me because I tried to quit like it was tough getting started, like it was not going well at all. And the reason I say it was good that there weren’t other options because I would have left. Like if fidelity would have hired me with some kind of base salary. And I know they wouldn’t because I interviewed there and they told me it looked like I quit everything like when it got hard. So that was kind of a tough.

But it was true.

John Corcoran: 10:56

Yeah.

Will Richardson: 10:56

So if I could find that dude that kicked me out of his office and told me I was a quitter, I would probably buy him a car today because a lot of good. Yeah. And and and it wouldn’t have been good if I had taken that job. So I think the reality was starting out in oh eight, oh nine. I mean, I remember calling people and sometimes they wouldn’t meet with me because they were worried about getting laid off.

I mean, it was a tough time. But it also was a time where people were curious about their financial plan and whether they ought to make any adjustments, or they were more open to ideas than they might have been in 2007, when everything was good.

John Corcoran: 11:33

Right. I want to know, you know, on the one hand, the kind of steady media drumbeat of like, news and information has gotten worse and worse. And, you know, if it bleeds, it leads, you know, the all the different media publications. They lead with kind of doom and gloom a lot of the time, which I know for you. Like you say, you shouldn’t get distracted by those sorts of headlines.

On the other hand, it does seem like that would open a door for you to have a conversation with people if you were to talk about that. Right. You know, like tariffs, like you need to make a decision now about your financial future because of, you know, this economic uncertainty, how do you rectify those two kind of tensions between those two things?

Will Richardson: 12:23

Well, it’s a great question. I mean, part of it is the media knows that our brain is wired to negativity. So they want us to click on stuff. And it’s not important to them whether John has a good financial secure retirement, that’s not their concern. They want you to click the ad.

And so there are things that are important to pay attention to. A lot of times for us, it’s about having the client know that we understand why they’re concerned about whatever the thing is. So it’s not hey, that doesn’t matter. Don’t change anything. Don’t change anything, by the way, is usually the correct response.

But we have to show that we understand the situation and why they’re concerned what’s going on. Now there’s exceptions. Like if somebody gets laid off well then yeah that that definitely changes things for them. They’re not going to start. They’re not going to keep adding to their investments.

They’re going to want to hold on to cash things like that. But a lot of the things are about understanding that there’s always going to be uncertainty. You know, the equity market is going to go down an average of close to 20% in a year on average in a given year, a good year, a bad year. That movement is normal, somewhere between 15 and 20%. It’s just that while it’s happening, it seems scary.

But we always find a way to the other, to the other side of it. So I think it’s important for us to demonstrate that we’re aware of what’s happening and why people are concerned, and then help them see that they’re well planned and that their plan was built to withstand whatever might happen.

John Corcoran: 13:55

Is that a big challenge for someone in your line of work? Is clients that are freaking out about the headlines and shouldn’t be.

Will Richardson: 14:07

You know, it’s interesting. So having started in 2008, there was definitely concern then. And the Covid, you know, 2020, you know it’s interesting that went down so quick. People didn’t have time to react in the way they might have if it had lasted longer. What I noticed was in 2025, that one really bothered people more than things that had happened previously.

And I think what we found was that there was some tension. Politically. And people who, let’s say people who did not vote for Trump were more worried about that than when I talked to people.

John Corcoran: 14:46

The conservative side of the perspective got it. So their political philosophy affected how they reacted to the turmoil in the markets in the spring of 2025?

Will Richardson: 14:56

Yes, and that was harder. That was probably the hardest one. I mean, remember, 2022 was a down year. You had multiple interest rate increases. And when I look back at that, people responded to that.

They weren’t excited. No one liked it, but they weren’t as nervous. So, you know, we.

John Corcoran: 15:14

Were the other half of your clientele were reacting to it in different ways, I guess. Right, right.

Will Richardson: 15:20

Yeah. Yeah. And so I mean, thankfully everybody, you know, stuck with their plan. We were able to work through things. And you know, there’s always going to be uncertainty.

But I will say that one, it seemed that it was bothering people more than most of the previous downturns that I can remember.

John Corcoran: 15:35

Yeah, yeah. Talk to me a little bit about the model, the, the kind of the business model because I don’t fully understand it. But Northwestern Mutual is kind of like the umbrella and you have your own like kind of basically your own company within that umbrella. How does that work?

Will Richardson: 15:51

Yeah. So everybody has their own profit and loss statement. And we pay to have an office in one of the locations. Northwestern mutual is located and they provide technology and compliance for us. So they don’t make anything in the sense of investment products.

They have insurance products that they create, and our clients have access to those insurance products, along with those from other companies. And from an investment standpoint, it’s it’s open. You know, we take on a fiduciary responsibility and they do as well. So what I like about that is that there’s nobody wanting to steer what kinds of products, so to speak, that clients are invested in. And so that our clients appreciate that.

And we do too.

John Corcoran: 16:37

Yeah. And it certainly seems like correct me if I’m wrong. The trend has been towards being a part of one of these larger financial Institutions, and it seems like there are fewer small, independent investment advisors that are not affiliated with a larger financial institution today.

Will Richardson: 16:58

I think a lot of times people start with one of the larger firms, and then sometimes they leave those organizations. And now what we’re seeing is you’re seeing a lot of private equity money come in to start to acquire some of these smaller operations. So it’s it’s interesting. It’s always it’s always changing. So ultimately, yeah, there’s there’s going to be things that you have to figure out, like where you’re going to get your technology support and compliance functions and operational capabilities.

And so that that tends to drive a lot of it for, for people.

John Corcoran: 17:29

Yeah. Now I want to ask you about you have had your podcast for quite a while. You do two internal podcasts and one external podcast. Talk a little bit about what the role that’s played for you in your business.

Will Richardson: 17:43

Yeah, it’s been really interesting. So about almost ten years ago I would listen to all the audio recordings from the various meetings that we have throughout the year, and that was what I did on my commute, and it occurred to me that more content could be created if we simply had conversations like what you and I are having right now and shared them. And because we get into detail about, you know, specific kinds of conversations that we might have with clients. It’s an internal podcast. So there’s one where I interview a different advisor every week.

And then the second one is a longer standing one with one other co-host, where he and I basically go back and forth on ideas of how to communicate more effectively as the the broad topic of that one.

[Continue to Page 2]
Pages: 1 2