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Sustaining Success with Trust in Yourself with Dan Weedin

heart & mindset mastery inspiring interviews & case studies starting a consulting & coaching business Oct 30, 2020

Bosses, colleagues and friends all questioned the wisdom of quitting his high-paying job and steady paycheck for the unknowns of starting his own consulting business.

After over 15 years of consistent and growing success - they now understand exactly why he did it. 

Dan Weedin is an author, speaker, consultant, coach, podcaster and founder of Toro Consulting, a firm that specializes in small business growth, particularly in the insurance/risk business. 

Dan is also a dear friend whom I have had the privilege of watching him turn his many ideas into profitable reality. He is an action-oriented visionary who deeply cares about people. 

Dan's path to the success that he enjoys today wasn't always a straight shot. He had some ideas that worked...and some that didn't. But sets him apart from his peers is that no matter what, he JUST. KEPT. GOING. 

You're going to hear a lot of actionable idea and inspiration from Dan in this interview that I did with him about his journey from just thinking about starting his own business to where he is now - using the power of his strengths and passion to make money and a difference...doing what he loves.

But of everything that he shares, the one thing that has stuck with me was the importance of trusting yourself and believing in your ability to learn and grow. 

Do you want to start or grow your own business?

Does fear about money or not having what it takes hold you back?

Do you struggle with owning your vision for your business with the guilt of now knowing how to make that vision happen?

If you answered "Yes" to any of these questions, you'll love my interview with Dan. Let Dan be your inspiration and guide and a powerful example of how to go after your dreams and achieve your full potential.  


Betsy Jordyn: Hey there, it's Betsy Jordyn and I am so excited to bring you today my good friend Dan Weedin.  And we have known each other – we just realized this – 11 years ago, right Dan?

Dan Weedin:  Eleven years ago we met in a bar and talked about Bon Jovi. 

Betsy Jordyn: We were at a business training where we were learning how to grow our consulting practices back in the day.  And Dan has done amazing things with his business, so he would support small business owners; he helps them in every aspect of the business plus a lot of emphasis on risk, is that correct?

Dan Weedin:  A lot of I would say risk strategy and emerging risk solutions which is one of my new brands.  That's what I do.

Betsy Jordyn:  And he's got a great podcast.  Do you want to plug your podcast too?

Dan Weedin:  Unleashed The Podcast.  You can go to UnleashedThePodcast.com, you can listen to all the episodes; it's also available on many different platforms.  I'll leave it at that, but if you to UnleashedThePodcast.com you'll find me.

Betsy Jordyn:  Okay.  So let me tell you why you need to listen in.  If you're a consultant or a coach or you're thinking about becoming one, and you want to figure out how in the world do I take my years of experience and turn it into a business, what can I reasonably expect from all of the ups and downs?  I really wanted to bring Dan here because he's been at this for a while.  He's been at his business for 15 years and he knows all about it.  And I think that there's something about learning from people who've been where we want to go that's truly inspirational, and Dan is an inspiration of what he's been able to do with his business.  But before we talk about what he's doing now more specifically as it relates to how he's growing his business, I want to take you back in time Dan if that's okay.

Dan Weedin: Um-hmm.  Sure.

Betsy Jordyn: Take me back.  I want to go back in time to 15 years ago Dan.  And he's working and what is he doing and what makes him decide you know I think I want to ditch this working for somebody else kind of thing and start my own business.  What happened to you?

Deciding to start your own business (2:03)

Dan Weedin:  Well I'd been an insurance broker for pretty much all of my career.  At that point it had been about 15-16 years that I'd been an insurance broker and I had made a good career out of it.  In fact you could say I was comfortable.  I was 41 at the time and had two children who were in high school getting ready for college.  And I went to my wife and I said you know, I'm not having fun.  In fact I'm really not having fun.  And it really kind of dawned on me that it wasn't the industry, it wasn't the business.  It was I really had grown tired of working for somebody else who was calling the shots, making decisions I might not make, and then earning money for them as opposed to earning money for me.  And then the final part was I actually thought there was more I could give but in the position I was in it wasn't possible; it's not what they wanted for me. 

This was actually about a 2-year period.  So I make it sound like it happened all overnight; it really had been going for a couple of years and I found myself getting to a  point that I was not having fun, I was complaining, I wasn't looking forward to my work.  So when I talked to my wife Barb about it, it was like she already knew that.  She knew that I wasn't having fun.  But the idea was okay; we have kids in high school, we have a comfortable living, and we're going to go from that to we don't know when you're ever going to get paid again.

That was the big step that had to be taken.  But once I came up with the idea of consulting, using the knowledge that I had gained over all those years in a way to advise people, to help people, the next step was okay, I'm going to burn the boats and we're going to move forward, and that's what we did.

Betsy Jordyn:  What I heard you say then is it sounds like a little bit of I'm not having fun.  Another thing is like wow, I'm working all these hours and I'm growing somebody else's bottom line was another thing.  Third is that you saw that you could make a bigger contribution than from the role that you had currently and you just – that was like the big things that were kind of going on in your that made you say I think I want to do something different.  Did I hear that right?

Dan Weedin:  You're right.  And they kind of piled onto each other because each of those three played a factor.  In an of themselves I'm not sure it would have led me to this, but the combination of such and the opportunity of the world we live in today.  Even in 2005 technology was starting – was a major part.  I don’t know that I could have done this in 1990 for instance.  So the availability to work from home and to create this was also there.  The combination all played a part.

Betsy Jordyn:  What's interesting is that you – like many of my clients, it is a 2-year journey or a 3-year journey.  Sometimes it takes a while to get there.  Was there like a moment that catalyzed it for you that you said you know what; I'm done.  This is the moment.  Did something happen that you said I really want to do this?

Dan Weedin: It's funny that you say that because there was.  And I don't know how it happened; I don't know what triggered it.  But in my head, I started thinking I wonder if I can make money consulting somebody in doing this.  So I had been selling insurance but then I started thinking.  You know I had so many – you know what?  I guess I know what did happen.  I had a lot of clients – not a lot – several clients over the previous 3 or 4 months who left me; not because of me but because there was a better product.  And they had actually come to me – that being said somebody gave me this proposal on commercial insurance – can you get these?  And I said no, this is a different market.  I don't have this company.  And they thanked me for my honesty and I actually had to advise them it would be better off if you went here.  It's a better policy; it's less expensive; it's just better.  

And then something hit me and I said I wonder if I can make money doing that.  I wonder if I can make a living advising people who have no idea.  And the only reason I didn't have them as clients anymore wasn't because of me.  My relationship was so strong that they felt confident in coming to me.  So that was – there was probably that moment in time where it's like okay, I think I can do this.  And from that point, it accelerated from the two years prior.  Within 30 days I had a corporation, I announced that I was leaving, I was moving forward. 

Betsy Jordyn:  So it's interesting.  It's like for a lot of people the discontent goes on for a while and there's like a defining moment.  And for some people, it's like they lost their job or something happened to their job.  But for you, you had some sort of vision that you were like I can make this thing happen, and so then you did it.

So then you also said that for you a big part of it was obviously getting Barb onboard.  Was it easy or is there something that you need to communicate; that you would recommend to other people around how do you get your loved ones onboard who are worried around how are you going to replace your salary?

Getting approval from your loved ones (7:43)

Dan Weedin: Yeah, you know I'll say for me it was easy.  Barb and I were high school sweethearts.  We had been together – let's see; we've been together now almost 40 years so even at that time we'd been together 25 years.  She didn't want me unhappy.  Now I had to kind of promise here we wouldn't starve.  But she trusted me and I appreciate that.  In fact, today she's working with me.  That's another part of the story for maybe another day.  But I had to kind of promise, yeah; I'll make this work.  I'm going to find a way. 

That's not – everybody's in a different situation and so that is a really important conversation.  Because being an entrepreneur for all intents and purposes, unless you have some other situation, turns off the money spigot.  And you may have some savings.  For me, I had money that I was going to be getting from the agency I was at for three years, and actually, it was enough to cover for three years to cover the mortgage, which I thought was a bonus because I wasn't even expecting that.  So it gave me even more confidence.  But you still have to eat, you still have to have lights on, you got kids going to school.  So that conversation with your spouse, your significant other, it's an important one because the money potentially will stop.  There are ways to accelerate that, but stuff happens like pandemics, a recession, that both you and I were consultants through.  Through no fault of our own stuff happens.

So you have to be prepared for that and you have to be very honest and candid up front.  And I think Barb and I, probably to our – we didn't know what we were going into.  We just had gone into a lot of unknowns together in the past and we were willing to do it again.  I'm not sure we knew exactly what was going to happen; maybe we wouldn't have done it, but I'm glad we did.

Betsy Jordyn: You know you bring up the important thing about the unknown because that is what keeps a lot of people stuck is that fear of the unknown.  And it doesn't sound like the fear of the unknown or the fear of can I make this thing work; it doesn't sound like that was a big tripping point for you. How did you get to that point where fear in any scenario – fear of money, fear of making it work – how did you get to a place where you weren't afraid?

Overcoming fear (10:11)

Dan Weedin:  I don't want to sound – I'll put it this way.  I trust myself implicitly.  I trusted myself and I didn't look at it as much of a fear.  There's a small fear of the unknown but I was actually more excited about what the opportunity was.  That was not even close.  The defining difference was I can't wait.  I can't wait.  I don't know what's out there but I can't wait.  And so I would say to anybody listening, you have to trust yourself so much that you're willing to put it all on yourself.  And that was part of the reason for the switch, you mentioned that.  I didn't like working for somebody else because I had to trust somebody else.  And I had to trust myself way more than I trust anybody else.  And you have to have that level of confidence to go into something like this excited rather than scared.

Betsy Jordyn: That is such a powerful thought around trusting yourself.  That sounds like because you trusted yourself then Barb was able to trust you.

Dan Weedin: Right.

Betsy Jordyn: And then your future clients can trust you because you trust yourself.  And I wonder how much they fear that so many people get riddled with is they don't trust themselves that they can manage through all of the difficulties. 

Dan Weedin:  Well this is part of the language.  I'm sorry for interrupting you; you know me well enough, I'm willing to do that.  It's all about language to yourself.  So if your significant other says to you or asks you, will we have enough money to survive; if the answer is "I hope so" that's a bad answer.  The answer has to be "yes".  How do you know?  I don't, but I will.  It's that level of confidence.  That's who follows – you know from a leadership perspective, even inside there might be a little bit of doubt you're going to project "yes"; we are going to be fine, we're going to be okay.  I will – and hopefully, we had a track record at that point that yeah, you know that we're going to be fine.  But that's the type of language and you have to believe it yourself in order to confidently and boldly say that to somebody else who's got a stake in it.

Betsy Jordyn: You know I was thinking about as you said trusting yourself.  I remember the first time I landed my first international client.  I’m going in another country.  I'm going into a brand new client.  I didn't meet anybody.  I landed this big contract with a company in a different part of the world, never met them before, in an industry I never worked for.  And I remember feeling like oh gosh; you had that like "oh crap factor" like I had that when I walked in.  And then it's like no, I trust myself.  I know what I'm doing.  And I was able to talk to myself very quickly like it only lasted a minute, and I think as I hear you talking about it is it sounds like that trusting yourself probably contributed to your career all along the way.  It's like yeah, I know how to do this, and you just keep drawing back on it.  And I think that's what's important for high achieving people who have a big career is you got results before; you'll get it again.  It's just in this whole new environment. 

The other thing I want to follow up with you on is something that you said is you burned the bridges.  I've heard you use that phrase before.

Dan Weedin:  I burned the boats.  Actually burned the boats.

Betsy Jordyn:  Burned the boats.  We talked about that before because you had I had a conversation about how important commitment is to your success and how that's the defining factor.  What does it mean to burn the boats, to you?

Commitment (13:51)

Dan Weedin:  So for those that don't know, it could be mythology but the story is when Cortez came to the New World they burned the boats.  And he said to his people, we have no way to get home; we're going to have to make this work.  While safety nets may sound okay, and maybe they are, I kind of said I'm not going back.  I'm planting my stake in this.  I have no boats to go back so I have to make it work.  And for me I think you have to have – I have to have; I'll just speak for me – I have to have that nope, there's no Plan B.  There's no Plan B.  It's Plan A.  And one way or another I'm going to have to make it work.  And I think part of this, and I don't know if you were going to ask this question, is while you have a lot of confidence you also have to educate yourself on what's new. I'd never been a consultant.  I needed to learn and I needed to learn fast.  And so that – having that level of having some coaching, mentoring, accountability, doing your own research – I learned very quickly that if I was going to burn the boats and had no place to go, I'd better get educated.  I'd better understand what it took because I was doing something different than what I was doing before.

Betsy Jordyn: So you equipped yourself.  So you were able to burn the boats because you equipped yourself and you weren't – a lot of the clients I work with, they struggle with that.  I should already know how to do this mess, and so they have a hard time asking for help.  And in someplace it's like hey, I don't know how to do this.  No big deal; I'll just go get the help. 

Dan Weedin:   Well and I bet most of your clients are experts on the methodology.  And you and I have spoken about this in the past; the methodology.  They're experts.  They could write the books, and maybe they do, on what they do.  But being a consultant and acquiring new clients is a completely different skill set.  It's a completely different skill set than the methodology.  That's what you have to learn.  And even though I had lived in sales, this was a different agreement; this was a different transaction.  Because when I was selling insurance everybody needed it; it was required of them.  Everybody didn't need my consulting.  They didn't have a budget for me.  And so that all of a sudden becomes a completely different level of marketing, of relationship building, of trust.  And that's what makes it different I think for a lot of consultants, probably many that you are coaching yourself, is you may be the world's greatest technology expert or greatest human resources expert or whatever; but if you can't influence somebody to hire you, you don't get to use it.

Betsy Jordyn: Well what I say is that kind of like what you here in your career isn't going to get you there as it relates to a business owner.  That you almost have to unlearn everything that you did about how you put your resume out to go find a job because the role that we want as a consultant or a coach is not on any org chart.  You have to find the role that you want, position yourself to go after it.  Which is why I call myself a positioning expert is you've got to position yourself and go after it, and you have to proactively advocate for your contribution.  Which is really different than I applied for a job.  It's a totally different kind of thing.  But I think that goes to the point where you and I have this in common is that we get excited about learning the new skills.  I love learning all of this stuff I have around digital marketing and how you make things work.  And whatever next I can learn is what I'm more excited about versus whatever I've mastered in the past.  It's why I keep reinventing myself.

You've been in business now for 15 years.  If you were going to look at the span of your business career – because you did it.  You were able to not only replace your salary but grow it tremendously.  You've done a lot of things right along the way so I'd love to hear what you would say are the best practices.  And I'm sure if you are like me you have a lot of expensive worst practices as well.  So if you could share a little bit about your best practices and your worst practices.

Best and worst practices (18:34)

Dan Weedin:  Funny, the worst practices come to mind before the best.

Betsy Jordyn: Okay, then start with – so what are the worst practices? 

Dan Weedin:  I remember – you know when I talk to the clients, I'll say this happened to me; don't let it happen to you.  I'll just give you a couple of both and we can go from there.  One of the biggest mistakes that I made early on was I often wasn't talking to the right person.  I would have conversations, great conversations; they loved me but they couldn't cut a check.  Even though I was working with small and medium-sized businesses, because it was in the insurance realm I might be talking to the person in the organization who was in charge of insurance or in charge of risk management.  And they loved that I could help them but they had no ability to hire me.  And then when we got to the point where oh, I need to get approval; well that other person did not have the same objectives or the same desire.  And so that was – it sounds like I should have learned it right away, but that's a slow process.  Are you talking to the right person?

The other thing that was – that took a long time too – these are not quick fixes.  But one of the things that was really important for me was to actually quantify the value that I had.  Because in my head it sounds good; it sounds really good if I say I'm going to give you increased peace of mind.  Good!  I'm going to make you more confident.  Good!  Well, what does that mean to my bottom line?  What does that mean to my profitability?  And it took a long time but I had to get to a point where I could actually put numbers to it; percentages to it; increases and decreases – whatever that number is, that became an important part of every proposal I had moving forward because people want to see; well how we quantify this?

Those are two areas.  That might even be a best practice.  That may turn into a best practice is in order to give your value; you may have tremendous value but it has to – depending on who your market is there has to be both qualitative and quantitative results and value.  That's a best practice right from the start. 

That's a quantitative one; here's a qualitative best practice that came out of – I think all of these came out of failures Betsy.  I think at some point all of these came out of something where I failed.  You have to make sure that you're always your best advocate.  Even if you have a significant other that is pulling for you, the words that you say to yourself, the self-talk; this is a hard job; it's a hard career to have.  It's rewarding but it's hard.  There's a lot of times where you can get down on yourself so that probably the best thing is that you have to cut yourself some slack.  You have to be able to be your best advocate.  It's okay to be down a little bit but you can't let it linger; you've got to go on to the next step. 

One quick note if you don't mind me telling just a quick anecdote.  You know this; I'm a golfer.  And I actually just recently – even though I've been golfing for 43 years I still go to a coach once in a while to get some lessons.  And I was voicing my frustration that I was having some bad shots and I was trying to fix them.  And he said something to me that turned into a business thought.  He said look; it's okay to have a bad shot and it's okay to be upset about it for a moment.  He goes but if you're trying to fix that bad shot with the next one you can't.  He goes  you know how to make a good shot; focus on that.  Focus on what it takes to make a good shot, not what you did bad before.  And I would tell everybody: focus on what you know it looks like to have a good communication style.  Focus on what you know how it looks like to build relationships, to build marketing campaigns, to build processes.  Don't worry about the mistakes you made; focus on what you know the right thing looks like.

Betsy Jordyn: It's almost like you just have to shake off the mistake and then start over.

Dan Weedin: Which is not easy.  It's hard.  That's I guess the one thing.  It's not easy but there's a mental toughness, and maybe more than discipline.  That's where the mental toughness comes in is you have to wipe that away and boldly move forward.  And that's a hard thing to do and it's something that I would recommend to all of your people; to practice that mental toughness. 

Betsy Jordyn:  One of the things I talk about with a lot of my clients is around how you achieve results as a consultant.  And a lot of people think well I'm here and here's my goal and it's going to be a straight shot.  And I say no, it's more like an ice skater; you move side to side.  That's how you move forward; it's like you're constantly pivoting.  And every mistake you make is a learning opportunity because I'll put that message out; it's like "well that didn't work."  But you got farther along because now you know that that doesn't work.  And then you get to move on and everything is a learning experience.  Now we can say that 15 years later that we've been in business, but it's hard at first because you're used to getting success in a particular way.  You're not used to failing as spectacularly as we might do in our own business.

Dan Weedin:  But that's the event, like life.  I mean that's like life.  I mean I think being an entrepreneur is so much like life because we have things thrown at us that – again whether it's a pandemic or a recession – and that's part of life.  And I think everybody's equipped to be a good entrepreneur.  As long as they have the coaching, the mentoring, the love of education and the resiliency, anybody can make a really good consultant if they have those characteristics.

Betsy Jordyn:  Would you say that those were the best practices is that you got your mindset straight, you invested in mentoring?  Are all those things the best practices that you would?

Dan Weedin: Yes.

Betsy Jordyn: Is there anything you would add to that list around best practices?

Dan Weedin:  I guess I would add this.  Be ready to – you just mentioned the word "pivot."  I look different now than I did in March.  I made some changes to my business because I looked at myself and said what happens if I can never leave my house anymore, for whatever reason?  And so I made some – do not be afraid to try to innovate.  In fact, it's a requirement.  You must consistently be looking to be innovative, to try new things, to fail at them, to learn from them, and to keep re-inventing yourself.  That would probably be the next, the other best practice I'd put in there.

Betsy Jordyn: As a wrap-up question; I've got one last wrap-up question.  If you were going to go back in time and were talking to 15 years ago Dan, or even 17 years ago Dan, and you were going to say one thing to him that would encourage him at that particular time of your life.  Now with everything that you know, what would you tell him that would encourage him throughout the journey and to let him know what's in store for him?

Dan Weedin: Wow!  That's a good question.  That's a really good question.  I think I would go back in an encouraging way and say there's nothing that's going to happen in front of you that is going to kill you; I mean from a business standpoint.  You can survive anything.  Just trust yourself even more than you trust yourself now; have confidence, have fun, and stay in the moment.  Don't worry about things in the future; stay in the moment and – this is about golfing – trust your swing.  Trust yourself.  And even though I said I did those things, I didn't as much as I could have.  I think I would go back and say hey; stay the course, you're fine.

Betsy Jordyn:  Wow!  Powerful.  Powerful words.  I love how you wrapped it back up with what you started with; is that this business is staying in and it is all about trusting yourself and trusting yourself to pivot, stay resilient and that you have what it takes and you can make this happen.  That's awesome!

Dan Weedin: Thank you.

Betsy Jordyn:  Well I am so grateful for this time, and I know it was super helpful for a lot of people who are listening.  If they want to get to know you a little bit more, well you have Unleashed behind you.  Do you want to just quickly explain that? 

Dan Weedin: Yeah.  Unleashed is a brand that I came out with probably 5-6 years ago – in fact, I actually registered trademarked the word – and it's really kind of a mindset of unleashing yourself.  I find a lot of people regardless of the type of business are fearful and they chain themselves to their fear.  I have a Jack Russell terrier that loves to be unleashed, and so Captain Jack and Bella were my go-to's on unleashing.  It's really about unleashing your mindset and getting rid of the fear, and being excited about going through the fence to find out what's on the other side.  That's where Unleashed came from. 

I also have a brand called Emerging Risk Solutions so I do a lot of work around risk strategy.  But my Website is DanWeedin.com and I'm [email protected]; I'd love to talk to anybody.

Betsy Jordyn:  And you do have your book out there, because your book does say a lot with that mindset.  If somebody needs some quick wins around the mindset and getting to the place where they can set themselves up. 

Dan Weedin: Unleashed Leadership, yup.  Thank you.

Betsy Jordyn:  Okay, awesome.  Thank you so much, Dan, and I really, really appreciate your time and thank you all for listening in.  I'll see you soon.

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