The Uncharted Route to RETIREment with Connor Oak from Work Optional

Brent Peterson (00:03.606)
All right, welcome to this episode. Today I have Connor Oak. Connor is with WorkOptional, and WorkOptional is a strategic partner of Entrepreneurs Organization Minnesota. Connor, go ahead, introduce yourself, tell us your day-to-day role, and maybe one of your passions in life.

Connor J. Oak (00:21.351)
Yeah, hi guys, Connor Oak here. Like Brent said, I work for WorkOptional, or a private wealth management firm based in the Minneapolis area, but clients across the country. I became a strategic clients partner, I think now, for it's been a little over a year. My firm did, so some background on me. I grew up in southern Minnesota, small town of Lee's Center, Minnesota. So everybody knows Lee's sewer from the green giant, the beans, and then Cambria. So I'm a town inland from there.

Growing up, like I said, I grew up with a different kind of entrepreneur mindset. I grew up on a farm, as well as my dad owned a concrete company and still does. So anytime I get sick of sitting behind a desk, I go down there and I'm quite humbled by what entrepreneurship means to those guys. So fast forward, I attended Gustavus Adolphus College down in St. Peter. Wasn't quite sure what I wanted to do. It was close to home, a very tight knit community. Got involved with the Gustavus Entrepreneurship Club that was started by

an ex-Deloitte partner, Russ Mikulets, who I count as one of my mentors, and has offered me plenty of opportunities to give back to Gustavus through entrepreneurship, and then what's called the Gusty Cup, think of a Minnesota Cup. So that kind of piqued my interest in entrepreneurship, but of course everybody wants to be an entrepreneur right away, I didn't candidly have an idea, nor had any really business acumen or skills at the time, so besides having a liberal arts degree. So after that I said the next best thing is I'm gonna go help.

entrepreneurs, business owners, so I took a job with an investment bank in Minneapolis here doing capital markets, M&A, follow on offerings. So I really was really in tune with business owners, working with them, what made them tick, how they grow their business, where they want to grow their business, needs for capital. And I kind of realized through some of my discussions with those business owners, guys and girls, guys and gals, that I wanted to be more on a personal side with them.

Um, so I wasn't quite sure what that meant. I didn't want to go to quite private equity. I wasn't a consultant build. Um, so I said, uh, what about private wealth management? What does that mean growing up? I had no idea what that was. Like I said, being from a town where, um, it was farming and construction were the main games. Um, so it just so happened to, I had a fun job in college. Uh, when Brent asked about one of my favorite passions is, is wake surfing, being on the lake. I grew up on the lake fishing, all that stuff. And I kind of took a liking to wake surfing, which

Connor J. Oak (02:50.079)
Wakesurfing is a water sport. You do it right behind a specialized craft. It's very low-impact, very easy, enjoyable. You can do it all ages. I've seen people who are 80 do it. I've seen people who are four or five years old do it. So through that passion, I worked at a boat shop, a Malibu boat dealer in Excelsior, and was introduced to the founder of our firm and his wife, Mark and Jamie. And Mark is also involved with EO and EOA.

as well as a strategic alliance partner. So through that, I went out, taught his kids how to, he had just bought a new boat, a bunch of stuff, wakeboards, water skis, surfboards, tubes, and I kind of went out and he said, well I don't know how to use this. So I actually, my foray into private wealth management wasn't some exhaustive search or interview process, it was I taught Mark's kids how to do water sports and now that I look back on it, it was more...

making the kids who were at the time, I think like seven, five, and three, comfortable with the water. And I think he took a liking to kind of, like I said, what I hope to give to people is a personal relationship, somebody that they can rely on, trust working with. Like I said, it's much more than working with stocks and bonds and paper assets. It's people's future. It's what their goal is, what they hope to achieve. So I've been with the WorkOptional now for about five and a half years.

And we recently, like I said, about a year or so ago, were kind of introduced, I guess it was before that, introduced to EO, EOA, through some of our current clients actually were past EO members, some are current members. And it's a very tight-knit group. Like I said, we're a small person team, so we're very curated with our marketing dollars and.

Like I said, you're not going to see our name plastered on billboards or any of that stuff. We really want to be able to help people versus just paying for some advertisement on a piece of paper. So through EOA, like I said, we've been involved with it. So we're a strategic alliance partner and Brent can probably give a better definition than I can of us what that means. But for what it means to us is helping entrepreneurs. Like I said, that's it. Everybody always kind of asks what's our typical client and I hate when people ask the question, well, what's your minimums of investing? Because that's the last thing that I think should be talked about.

Connor J. Oak (05:08.587)
What are your goals? Are we a fit? Where do you want to go in life? And like I said, what do you want to achieve? So I feel like we're just scratching the surface with EO and EOA and everybody's been very receptive to us. And like I said, we hope to be a very good value add for the broader organization.

Brent Peterson (05:27.186)
Yeah, thanks for that introduction. I wanted to find EO versus EOA really quick for the listeners that may not know. Accelerator is EOA and that's business owners and you have to be, to be an entrepreneur's organization, you have to be an owner or a co-founder or a former founder, but so Accelerator is revenue below a million dollars and more than a quarter million and then Standard EO is over a million dollars. So that's, that's kind of the.

Connor J. Oak (05:31.244)
Thank you.

Brent Peterson (05:55.53)
That's how they see it as a definition. And then some chapters have different thresholds as well, 5 million and above and 10 million above. But the standard there is those two levels. Tell us a little bit about work optional and how it's maybe unique to the entrepreneurial space. I think a lot of the other wealth management's cater to.

everybody, it's sort of vanilla we call it, you know, in the industry. Tell us a little bit about work optional and how it caters to entrepreneurs.

Connor J. Oak (06:31.123)
Yeah, so work optionally, like I said, it was, I'll kind of give a back story from Mark on why he started. He actually had a job painting St. John's and St. Ben's, the school in the summer. It was a summer job for him and he made a little bit of money and he said, hey, I want help. So he went and found an insurance agent and a state planning person and an investment guy. Well, he received bad advice all around and it really kind of stuck home with him. Like, hey, I was asking for help.

or I need help I just don't know where to go. So that was 20 some years ago in 1999 and he kind of founded the firm and really wanted to take, like I said, it sounds wealth management can be a very vanilla business. Like I said, there's a lot of the big players in the names, the Merrill Lynch's, the RBC's, the large TD Ameritrade groups and stuff like that. We take a different approach being an RIA, which is a registered investment advisor. So.

We're not a branch of one of those that I just mentioned before. We're independent. And I think that's pretty important. And I encourage everybody, all the listeners and stuff to look up what a fiduciary is. And fiduciary means being in the acting and performing in the best interest of your clients. And you think that would be everybody, but when you really kind of get into the details of it, it can get pretty mixed up, especially in today's world with.

the influx of cryptocurrency and AI and all of that stuff. I think true wealth management is taking a holistic approach. As I started on the call, it's much more than paper assets. It's tax planning, it's retirement planning, it's estate planning. We look at all of those things as returns as well, similar to what's on the paper. So saving clients money on taxes, I mean, one of the first things that we like to do is...

not ask the client, hey, what are your investments? Let's see your tax return. Let's see if we can add some immediate value there. Let's look at your company benefits. Let's look at your 401k. And a safe plan is a huge piece. People build great legacies, and they want to pass it on, and they want to be able to enjoy it and not have to worry about it. So that's really where we come in, and I'll say act as a personal CFO. Of course, we do manage the paper assets and stuff like that. And I think we have a very good, strong platform that we do for that.

Connor J. Oak (08:52.811)
And like I said, we don't represent any products. So I think, like I said, taking the holistic approach and when you look at our typical client, it's everybody from somebody who's just starting out, a firefighter and a nurse, all the way up to people who have had large eight, nine figure business exits. And I think, like I said, we look at them the same. And I think I draw a lot on my past, working for my dad and working for my uncle on the farm. And there's a lot of parallels with entrepreneurship for.

that group of people as well as somebody who might, like I said, be running a 200 person business or an EO member. So I think just being a value add in any, we've had clients call me from car dealerships saying, hey, is this a good deal? Should I finance it? Should I pay cash? Please help me. So I think that's where I really feel like we can be apt for our clients. And I know, like I said, you would think.

We have clients who are CFOs of large companies, and you'd think that they'd be able to manage stuff themselves, but they look at it, like I said, from a full picture. If something happens to me one day, I wanna make sure my wife or my husband is taken care of. So I feel like we get a lot of people who get comfort in knowing that, hey, we're here. We're just a phone call away. We're a small team. We don't have thousands of clients. We don't have sales quotas, none of that stuff.

Brent Peterson (10:13.414)
I want to dip into that younger entrepreneur. At one point I was a younger entrepreneur and the last thing I thought about was wealth management. And I wish everybody says the best time to start is 20 years ago and if you haven't done it then start today, right? Tell us, talk a little bit about that, you know, sort of even before the accelerator phase just as you're getting into it at least from a planning standpoint and starting...

Connor J. Oak (10:31.304)
Yes. Yeah.

Brent Peterson (10:41.402)
and start to talk to somebody like WorkOptional, how important that is to get that ball rolling as soon as possible, no matter what phase you're in.

Connor J. Oak (10:51.187)
Yeah, and I think that's a great way to start is, like I said, you're never too early to start with wealth management. And I say wealth management as people think. Again, I go back to paper assets, how much do I have to invest? Here's what I can retire on. There's so many software programs, plug this in, get this return, here's how much you're gonna have. But I think at the start of it, it's setting up, should you be a C-Corp, an S-Corp, you have a business partner, Articles of Incorporation, what's a buy-sell agreement?

Stuff like that. So it's all those little pieces that oftentimes when you're starting out it gets overlooked because like I said You're trying to build your business and I think like I said, we don't act as somebody who gets in the way of that We like to run parallel with our clients So I think from the onset it's being able to help them with like I said you your best Ability is to run your business. Let us take care of everything else or at least show you the tools Oftentimes, I think that's one of the great things about EO is

for some of the younger entrepreneurs that we've dealt with since being part of EO and EOA. Even ones that are not part of EOA or EOA yet, who we've said, hey, this is a great organization, go check it out. But before that, it's just a network of people. The people that help with traction, the EOS implementers, the corporate finance attorneys, the business insurance people. I think there's a lot of value. We can spend hours and hours.

with somebody talking about that. And I think it all starts with the vision. What's your vision? And then let's work backwards from there. There's no canned formula. Like I said, every day I come to work and I feel like an entrepreneur, even though, like I said, I'm not one technically on the speaks, but I get to advise people and I get to see, and I think whether it's a young entrepreneur or an older entrepreneur, we learn so much from our clients that it's really a true.

working relationship right from the get-go.

Brent Peterson (12:48.982)
Yeah, talk a little bit about how you can share, not specific experiences from other clients, but you get knowledge about their experience that you can pass on and share with other clients that are in the same space or even different spaces as long as they're, if they're running a business, there's always commonalities.

Connor J. Oak (13:09.267)
Yeah, yeah, I think it's a lot of it is employee management. I think between COVID and work from home, I mean, I'll be candid. The firm is made up of people who are, let's say, north of 45 years old. I think Mark is the oldest and he might be 51. I don't quote me. If you listen to this, I'm sorry, Mark, if I dated you, but me being 28, I like to think that I'm on the forefront of technology and uses, but I think it was exasperated by COVID.

Clients are saying, hey, look at this tool, look at this tool. And we were able to incorporate it within our business and share it with other people and more act as troubleshooters for some of the Zoom technologies and stuff like that. But I think besides that, learning employee management, like I said, I look at our clients as family. So a lot of people, like I said, we can be a psychologist at times. So just drawing on specific.

experiences, like I said, there's the common themes of just being upfront, being vulnerable. I think vulnerability is a huge thing that we've been able to take from our clients and share it's okay to be vulnerable. Ask for help. There's never a dumb question. So I think those are probably the biggest things right off the top of my head. Like I said, if you gave me 10 minutes on pause, I'm sure I could write a list that would fill up a notepad.

It's something new every day. Like I said, that's why it keeps it interesting.

Brent Peterson (14:35.218)
We talked a little bit of entrepreneurs organization Minnesota, but entrepreneurs organization is a global entity But the entrepreneur twin cities like there's no there's not one thing that encapsulates everybody, right? So, you know your goal at work optional is not just to serve entrepreneurs organization, but to serve the broader scope of entrepreneurs Nationwide talk a little bit about how

Connor J. Oak (14:42.518)
Mm-hmm.

Brent Peterson (15:03.67)
Maybe talk a little bit about how being a strategic partner with entrepreneurs organization has helped you to better connect with other entrepreneurs even outside of the EO organization.

Connor J. Oak (15:18.911)
Yeah, I think within EO, some of the, and I'll say more EO-A as well, the quarterly learning days are, I'll try to do my best explanation of that, are days where all the entrepreneurs get together and kind of go over a discussion topic. It might be strategy, it might be cash flow. We've been able to learn from a lot of very smart people who have been entrepreneurs, who are in the process of it. And...

different strategies, like I said, cash flow, insurance needs, liability protection, and stuff like that. And we've been able to take that to other entrepreneurs and say, hey, this is something that we've maybe just talked about high level, but now we feel comfortable enough in a meeting or over a lunch or over a coffee, let's dig into this. And let's see where this ends up for a client. And I think that's probably been the biggest value added is, when we came into EO or EOA, like I said, we have some clients that are.

current clients that are past EO members, whether they've sold their business and just decided, hey, I've been in it for a number of years, or clients who are just building their businesses and being able to, like I said, lean on them a little bit, but it was a new organization to us, but we've been welcomed with open arms. So I think just trying to immerse ourselves, but also, like I said, knowing our role is not to overtake conversations, not to sell the work optional brand, it's just to be kind of a.

sounding board for all entrepreneurs in general.

Brent Peterson (16:47.542)
You had mentioned earlier, smart, right? And I can say that I joined EO as an accelerator back in 2015. And it took me 20 years to decide or realize that, hey, I don't actually know everything. I think a lot of entrepreneurs, no matter what the age, feel as though that they know everything. And they oftentimes don't look at other resources to help them grow their business, right?

Connor J. Oak (17:02.659)
Yeah.

Brent Peterson (17:15.966)
And I think the biggest thing, really what sparked this was that learning day. And my very first, my introduction to entrepreneurs organization was a learning day and I went to that and I'm like, oh my gosh, this is like, what? I get all this and it's part of my membership. Um, I knew that learning day, if I were to go to some conference, just that one day would cost me as much as my year membership in, in EOA.

Connor J. Oak (17:32.477)
Hehehehe

Brent Peterson (17:44.254)
Talk a little bit about how you help entrepreneurs grow by educating them on especially wealth management, but you've talked a lot of other things just helping them decide on should I be S-Corp or C-Corp or just at least helping them understand the differences within that financial realm that even though you think you know everything, you can never know everything and a group is always better than a single entity.

Connor J. Oak (18:12.939)
Yeah, yeah, I think, like I said, where we can really, once we kind of, I think, understand a client's, or I'll say an entrepreneur or a client in general, what their vision is, then like I said, we'll work backwards from there. So depending on where we've had clients in all different stages of their business, and I've always felt that we've been able to add value in some component, like I said, whether that's a business strategy piece, when they come to us, sometimes it's, they're having...

personal problems, issues at home, issues with their marriage, being an entrepreneur, like I said, can put a strain on a lot of people. So like I said, I think what we're really good at with entrepreneurs, and I'll say our clients in general, because I'm sure there's some people that hopefully will listen to this that aren't necessarily entrepreneurs, but they're looking for help or maybe I haven't seen that, is constantly having touch points with them. Just reaching out, asking how they're doing, is there anything in their personal life, professional life that's bothering them?

Or they want to, I mean, we get it all the time. I saw an article about this. What do you think of this? Is this something we should be looking at? So I think that's what you talk back to what we learn from clients. Since COVID, and I'll say since 2017, there's so many new tax strategies that are new, the ever-changing IRS regulations. So I think that's where clients look to us to say, hey, you know what? I don't want to go dig through.

the IRS website or I don't want to get on the phone with them. I want you to educate me. Give it to me from the 30,000 foot level and make sure I understand it. So like I said, I want to be bulletproof. And I think that's our job is we don't want any surprises, at least not bad ones. But I think when we really get in a groove with entrepreneurs, and I'll say it, you're not going to decide if it's good to work with us or our firm after three meetings or.

a couple hours sitting down over coffee or even at a social event. We like to look at, like I said, not necessarily the returns on paper, but hey, here's where you were when you joined WorkOptional or you partnered with us. Let's look at you at 50. I mean, we have clients that have been with us now for north of 20, 25 years. And it's fun to look back at all the old notes and hey, why did we do this retirement plan versus this retirement plan?

Connor J. Oak (20:33.163)
kind of look back on all the progress that we've had. Because like I said, there's a myriad of components within wealth management. And sometimes you get lost just in the, hey, I opened my statement and I'm down this month or I'm up this month. It's, hey, let's look at it at the long-term trajectory and see where we end up and see if what we made was the right decision. And if it wasn't the right decision, let's go back and revisit it. What would we have done different? So I think just being candid with clients is, like I said,

probably the most important part of how we grow with them.

Brent Peterson (21:06.506)
I'm going to close out the podcast today with not advice because in EO, an entrepreneurs organization, we don't give each other advice, but we share our experiences, right? And I want to challenge, I want to give you a little bit of a challenge. We didn't prep this. I want to call it the experience blind spot. And I think that in wealth management, there's so many things that people don't know that they should know.

Connor J. Oak (21:13.901)
Yeah.

Brent Peterson (21:32.578)
that they could know but they don't know because they don't know and they wouldn't know unless they ask somebody else, right? I said a whole lot of contradictory words there, but there's a blind spot that people have that they could learn when they reach out to somebody who's an expert in that space. Give us a blind spot that, just on top of your mind, that you've seen that has helped other entrepreneurs move forward in their financial world.

Connor J. Oak (21:38.582)
Yep.

Connor J. Oak (22:00.735)
Yeah, I think one of the ones that comes right off the top of my head is taxes. Um, and I know on this podcast, we talked about tax strategy, stuff like that. But for all of the entrepreneurs, business owners listening to this, one of the, it's crazy because like I said, um, everybody makes mistakes, but within CPAs, um, and people who prepare taxes, oftentimes every single year, we find that, uh, um, when you pay us a fee or you pay different fees, a tax preparation fee,

the CPA or the accountant will miss writing that off. It's a simple, whether they charge you 500 bucks, $1,000, that's an immediate, like I said, that should be, so I'll say that's probably one off the top of my head. More in depth is 401K plans. Oftentimes we have clients that are getting killed in taxes. However, if you pull back some of the onions and you look, well, they've been doing Roth 401K contributions versus all pre-tax contributions.

So little things like that, I would say. The broader realm is tax strategy. Like I said, I can tell pretty quick if somebody is underinsured or wants to need, has an estate plan. And I think, I guess, one other thing I want to mention around estate planning is making sure you have beneficiaries on everything. We can do our jobs great, but if you don't have a transfer on death deed for your house or a pay on death on your bank account or beneficiaries on your 401k plan.

We, our jobs kinda, it makes it hard when all of a sudden you get into probate. So I would just encourage everything. Those are some of the little nuggets, like I said. We're happy to get into the weeds of people. Some people like it. Some people say, hey, hold on, that's enough for today. And we always tell our clients, usually by the third or fourth meeting, have a couple aspirin when you come to us, cause we're gonna throw the kitchen sink at ya. So those are just a couple of things, but like I said, I could go on for forever. So I encourage anybody that has a question, like I said, I hope this at least gets somebody to look at one of those things.

and say you know what I took a nugget from this so.

Brent Peterson (24:02.486)
That's awesome, thank you. So one challenge that there is for all of our strategic alliance partners is there really is a no solicitation policy within entrepreneurs organization. So it's not a challenge to connect with other entrepreneurs because there's all kinds of ways to do it. But I wanna give you an opportunity to just do your, to tell us, give a couple of minutes, talk about work optional, how they get in touch with you, and maybe some of the benefits, why they should talk to you now rather than next spring.

Connor J. Oak (24:28.588)
Yeah.

Brent Peterson (24:33.122)
the reasons, you know, just give us a short little pitch and we'll close out the podcast with that.

Connor J. Oak (24:38.451)
Yeah, no thanks for that. I would say like I said, Reach Out, we're very approachable. We have an office up here in Plymouth, so we try to be out and about. You'll see us at different events that we support, charitable events for different organizations, a lot of the city municipalities, so look out for us there. Like I said, you're not going to see our name plastered in the Star Tribune on Sunday, we're not going to have a TV show. I try to stay active on LinkedIn, so people like Brent help me.

Hopefully I'll be able to share this podcast or something and maybe get a little bit of visibility. But you can reach our website is just workoptional.com. You'll find the whole team there. My name is Connor Oak. Hopefully, like I said, I'll print, you can share my email or my contact information. But I think that's probably, like I said, the best way to reach out for me. And I'd say, like I said, everybody likes to put it off. It's easy to put it off, just like it's easy to put off filing your taxes. But...

I still think there is still time between now and the end of the year for a lot of year-end tax planning and tax strategies that if you have a question about that, like I said, we don't need to do the whole full suite of financial planning and advising. Let's tackle, let's block and tackle what's right in front of you. I think for entrepreneurs, that's pretty important. There's this one issue that's just kind of holding them up from kind of opening the flood gates. So I think that's where we can, like I said, we're very approachable. We call us any time of the day, like I said.

We probably should not work on weekends like everybody says, but we do because like I said, being an entrepreneur doesn't stop. So I think one of the overarching themes of our firm is reliability. People inherently value reliability. You rely on your car to get you from A to B, phone connectivity, high speed Wi-Fi. So I think like I said, we want people to be able to rely on us. And I think that's what makes us.

Brent Peterson (26:28.046)
That's great, thank you. And I'll just put a little plug in there. It is WorkOptional, right? That's the name of your firm. And yes, WorkOptional, as an entrepreneur, sometimes it's, thinking about that helps them to understand that work is optional. And we oftentimes do end up working seven days a week and WorkOptional, taking a break is always important as an entrepreneur. And you know, WorkOptional's there to.

Connor J. Oak (26:34.783)
Work optional.

Connor J. Oak (26:49.603)
Yeah.

Brent Peterson (26:57.334)
kind of get your back in terms of making sure your finances are in order and that your wealth is growing over time without you as an individual having to spend seven days a week trying to manage that.

Connor J. Oak (27:12.959)
Yeah, absolutely. No, I encourage anybody who has, like I said, who has a need or just really wants to talk about wealth management. I mean, hey, come tell us that we're, I know, like I said, wealth management gets a bad rap sometimes similar to insurance planning and estate planning, but I do believe it is necessary and it's even more necessary for entrepreneurs. And like I said, that's where I like to feel like we slot in and add the holistic value.

Brent Peterson (27:37.782)
That's great, Connor. And I will, I should add, I should have started. I'm a client of Work Optional. And so I drank the Kool-Aid. It's not Kool-Aid, it's just regular old good water that helps you grow and move forward. Thanks, Connor. It's been such a great conversation. I appreciate you being here today and I hope you have a warm and productive weekend.

Connor J. Oak (27:42.596)
Yeah.

Connor J. Oak (27:54.539)
Yeah, thank you for that, bro. Yeah.

Connor J. Oak (28:02.387)
Thank you for the inclusion. I don't know if I'm as warm as you are right now, but hey, we all have to work for something so Thanks, friend

Brent Peterson (28:10.134)
Thanks, Connor.