¶ Personal Growth and Professional Success
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We look forward to working with you To our listeners . That's it . Let's get the show on the road . Welcome back , friends . Welcome back to another episode of the Freight Pod . I'm your host , andrew Silver , and I am joined today by no one , all by myself .
Singing is not the way I should be starting this episode , but I am trying something new episode , but I'm trying something new , and this is something I've struggled with , struggled to get myself to follow through on .
For literally months , maybe six months , I've been thinking about trying to do episodes by myself , where I come and I shed light on things I know about or specific topics that I'm seeing in the industry , whatever it may be , and it's just something I don't know why , but I've been so scared to do and ironically so .
To take a step back , I'm in an interesting point in my life where I found professional success in starting a company , growing that company and selling it , and I think that a lot of people think that when you have that trajectory , that's like the top of the mountain , so to speak Growing a business , selling it and making money Like I think , for me at least .
I thought that would feel like the top of a mountain and it hasn't quite felt that way . In some respects it has . In some respects I'm incredibly I mean I'm incredibly grateful for what has come from that the financial windfall , the freedom it's given me to do other things now , but I think , a big challenge that I've always had in my life .
When I think , dating back to when I first started working when I was 16 , my personal life's always been a mess and I was a troublemaker as a kid . I had issues with Tourette's I didn't know this until a few months ago , but I had ADHD and I just always found myself getting in trouble and I was someone who they'd consider a smart kid who was capable .
I was one of those people who was telling me you have so much potential , don't ruin it . You have so much potential , stop getting in trouble .
But school didn't really resonate with me the way that work did and I don't know why I was so attracted to doing bad things , whether that was sneaking out of the house when I was 14 to meet friends and get drunk with booze we stole from our parents , or I smoked a lot of weed throughout high school . I gambled a ton , bet on sports , played poker .
A lot of my personal life I spent , I don't know , chasing something .
That was not healthy and I told myself at some point I don't know why , I convinced myself and I maybe have spoken briefly about this before , but we'll go a little more depth here but I convinced myself that as long as I was successful professionally , it was okay that the rest of my life was in disarray and as long as I was working hard and making money ,
that was what I was focused on . I was so focused on achievement and professional success that it became an excuse for the rest of my life to be in disarray and perpetuity . Throughout my 20s , my 20s were chaos . I mean , I was partying . I look back and want to say I was having a good time . But I don't think I was .
I think I was masking some trauma or challenges I was dealing with self-created . I believe that it looked fun . I had a lot of friends , a lot of friends from work . We'd go out on the weekends , we'd go to the bar , we'd party and at the same time I was successful at work . So it always looked and felt like this is okay .
You're enjoying your 20s as they say . You're enjoying your 20s as they say , but I didn't develop , I guess , a fulfilling personal life . I don't know that I ever developed a strong value system that was written in stone , so to speak .
I think I have a value system that I roughly understand I want to do good in the world , I want to be a good person , I'm focused on my family , things like that . But if you were to ask me what are your values ? I don't know that I could easily recite them for you right now . I'd have to sit and think about it a little bit .
And I say all that to say that I'm 34 years old today and I was fired from my job . The company that I built with some amazing people we built in March of 2023 . It's been a year and a half , it's been over 18 months , and I think I'm finally starting to figure some things out . I said at one point I wanted to be grateful one day that I was fired .
It stemmed from a Stephen Colbert quote that was really deep and focused on kind of the idea that to be human is to experience suffering and to experience pain , and it's important that we're not just grateful for the good things , but we're grateful for the hard things . We're grateful for the things that mold us into better people .
And I think for a lot of people , if they had been fired from a company that they had just sold and made good money on , I think they wouldn't have found themselves in the type of disarray that I found myself in .
And that's because I don't think a lot of people have had the path that I've had , one where they do focus so much on their professional success that they allow their personal life to live in this constant state of disarray . I've had to cut a lot of things out of my life . I barely drink anymore . I don't do any of the drugs that I used to do .
I don't gamble anymore Things that caused problems in my life . I just don't mess with anymore , or I try not to . I still mess around with marijuana , still take edibles and I maybe make an excuse that I think that's helpful for me . I've seen creativity through some of that , but I just have had a lot of time in the last year and a half to reflect .
I started seeing a therapist that I've now been with for over a year . I'm proud of myself for sticking with that for a year and one of the things that as I was really struggling because I couldn't find purpose like that's . I think the essence of what's been a challenge for me the last year and a half is I lost my access to my business .
The thing that I was carrying is part of my identity . As I lost that , I felt like I didn't know what I had . I didn't know what I should be focused on . I didn't feel like I had something to wake up every day and be excited about or to be thinking about or contemplating ideas for .
I was just waking up and trying to figure out what to do and I found myself in a somewhat depressed state for quite a while . That I'm working my way out of and I think the thing I want to talk about today is rooted in the idea of the concept of just do it , which Nike's slogan , which , ironically , people probably don't know this , but just do it .
The slogan came from a death row inmate . Whoever was in charge of Nike's marketing or borrowed that slogan or was inspired , saw a I believe it was a quote from newspaper or something where a death row inmate was asked for his final words and he was like just do it , let's just get it over with . Let's take the step and move and go .
Interesting for that to then be the cornerstone of all of Nike's marketing for the next I don't know 30 years or however long they've been doing that , but that's a side
¶ Inner Struggle and Self-Discovery
note . My point , though , about just do it is as someone who has struggled a lot in their life with self-worth and feeling like I am worthy of connection and love and all the things that all of us humans are worthy of . I don't know why this has been such a struggle for me for 34 years , but I think a lot of my life .
Maybe this has to do with spending so much time doing things I shouldn't be doing . That I started blaming myself as a kid .
When you start smoking , weed and drinking at 13 years old and you're hiding it from your parents , and you start gambling and playing poker and hiding it from your parents and all these things like these actions , you start to feel bad about who you are as a person , and I think that's maybe what drove some of why I felt like I was a bad person or undeserving
. I also think it maybe had something to do with having Tourette's as a kid . You know where I would be twitching and blinking and shrugging my shoulders and coughing , making noises when I shouldn't Like .
I distinctly remember being a 12-year-old kid in school taking a test and my tick at the time from Tourette's was this like little cough , like I would do it every 30 , 60 seconds . I mean it was a . It was annoying . I'm certain it was annoying for anyone who had to be in in space with me or in a class with me .
And I just remember a kid while we're taking a test and I'm like I can't stop doing that , and he just turns and says will you shut up ? And like that was a little bit of my childhood . And I think when you're young and you're different , you question like why me ? Or did I do something to deserve this ? Or am I a bad person for this ?
And you know I don't think I had a healthy outlet for communication . I don't think I really processed some of this stuff as a kid and , as a result , I just think I lived in my own head with it and told myself I was bad , told myself I was unworthy and undeserving . And if you do that for long enough , you believe it .
And when you believe it it's paralyzing . So the reason that I wanted to talk today in this light there's a couple of things . One of the things comes from my therapist . A few months ago , as I was , she said to me she said , andrew , I think you will start to find some happiness if you really focus on the things that are your quote , unquote superpowers .
We all have superpowers . We all have something one , two , three , four , whatever number of things that we are exceptional at . That we are naturally inclined to be good at . And once we figure that out , we start to do it over and over again and it builds that skill until it becomes a superpower .
And for everyone it's different and some people are like really , really exceptional at something . Others are just like great at it . Whatever it may be , but it still is ours . It's the thing that we are great at . And she asked me to spend some time thinking about that . Like , what is it that you think is your superpower ? And I have .
I'm not someone who believes in signs , necessarily . Yet my therapist is trying to get me to believe in this concept .
She's having me read this book from a woman named Gabby Bernstein the Universe has your Back , and in it there's a lot of these kind of trust the universe , trust the signs and I'm not there yet spiritually , but bear with me as I kind of explain this .
So a week after she told me that and I've spent time now thinking about , like , what is my superpower , what are the things that I'm really good at ? I went out with some old coworkers for someone's birthday and we were at the club .
I wasn't drinking , I just was hanging out , which was a weird experience because I used to go to this club all the time and just get absolutely obliterated , make a fool of myself , but it was interesting to be the sober guy hanging out with 20 people getting after it , having a good time .
But one of my old employees pulls me aside and I hadn't seen him in six months or something like that , and he just was like we really miss you . And I think that the thing that we miss the most is your ability to connect with people en masse , your ability to connect with people at a large scale , regardless of who it is .
You have that ability and you demonstrated it throughout your time at Molo as our CEO . When you would give speeches , you would find a way to connect with all of us at once , and that was something that I think we all really appreciated . And so I was sitting there , you know , really grateful that he was sharing this with me .
And then I started to think like , is that it , you know , is that my superpower ? Is that the thing that you know I'm great at ? And when I think back to my time at Molo , the thing that I got the most , that filled my cup the most , was my company speeches , which I did every two to three weeks .
For most of the time , while I was at the helm , I would do these kind of State of the Union address speeches to the team . It'd be 15 , 20 minutes long . The purpose was typically to rally the troops , get people excited and motivated , but also to communicate and articulate what was going on in the business . It was a storytelling opportunity .
I always tried to tie stories of what was going on in our business at the time to the vision right .
So for us , we were dead set on creating the best experience in the industry for our people , for our drivers and for our shipper customers , and so I would spend time during the week talking to teams and understanding , hey , like okay , did we just won this award ? Anheuser-busch named us Carrier of the Year .
Okay , great , let's talk about that in a meeting and then thinking about , like , why did we win that award ? What is a story that I can share with people that explains that , by following through on who we want to be , that led to us getting the results we were looking for ?
I think I remember one example so perfectly regarding Emily Madden , who was like Molo's I don't know sixth , seventh employee , maybe ninth one of the first and one of the best , and she was leading our operations team at the time . So she had a ton of responsibilities and a ton of accounts . She didn't have any accounts . She was personally managing .
She was managing probably 50 or 100 people , whatever it was . She didn't have any account . She was personally managing . She was managing probably 50 or 100 people or whatever it was .
And on New Year's , on December 31st , we had a ton of orders for Anheuser-Busch that had to get out and Emily was up until , I want to say , 2 o'clock in the morning providing updates to Anheuser-Busch and they were so appreciative and so grateful and she had put her own personal interests aside on a holiday to do what was best for the team and tying that
story in to a speech to the company around . Why did we get named Care of the Earth ? It's because of things like that , and so my point in bringing that up is I want to do that more . I miss it . I miss flexing that muscle , so to speak , of being in front of a group and articulating a message in a way that connects .
I knew when I started this podcast that that would create an opportunity for me to do that , but that was over a year ago and I've yet to do it . It's because I'm scared , I'm worried , and the reason , frankly , is because of self-doubt , self-doubt .
I like to think that in my brain there's a constant boxing match going on between two versions of myself and , to simplify it , one version is the hero , the other version is the villain . The hero believes I'm a good person and he believes in me .
He believes I'm capable , he believes I'm worthy of love and connection and that if I'm willing to do something and put my heart into it and and give it all I have , that I'll get it done and then I can do good in the world . The villain is an asshole , frankly , but he is everything that is self-doubt .
He is everything that is telling me you're not good enough . Don't do it , you're an idiot . Nobody wants to hear what you have to say .
That's real and it's a never-ending boxing match in my brain that is constantly going on and when I wake up in the morning it's a question of who's currently winning the fight and it feels like the good guy's usually winning , but sometimes the villain creeps in and gets a good blow on a good right hook , so to speak , and it'll completely ruin my day .
I like the notion of staying in the fight . When I think about all of the good I've done in my life , it all started with the idea of just doing it , of just freaking starting , get into the fight and then stay in the fight .
¶ Overcoming Doubt and Taking Action
When we started Molo , we had no idea what we were doing . I knew how to broker loads . We had no idea what we were doing . I knew how to broker loads . I had spent five years as a carrier rep . I had spent one year working on site at Kraft Heinz as an operations rep in their transportation center . I spent two years working in Denver opening an office .
That was my first time leading or managing people and that was also my first time kind of running a sales group on the customer side . So I'd done the primary functions of brokerage but I had no idea how to run a freaking business . My partner , matt Fogarty , had no idea how to run a business .
He was a basketball player who then went and worked at IBM and was successful , very , very smart , one of the smartest people I know , one of the most capable . But when I looked at our deck the original deck we made for what was then called Simba Transportation , it was a seven-page deck .
The first page said Simba Transportation a stupid name we'd come up with . The second page said our team and it was a picture of me with a bio about me and a picture of Matt with a bio about him . And the next page was our value prop . And the value prop was not that compelling . It was not . I mean , it was pretty simple and straightforward .
But we weren't coming in with some new fancy technology . We weren't coming in with like $500 million that we were going to use to subsidize everybody's freight costs , to be the fastest growing broker ever .
We were just coming in with the idea that we could outwork people and that if we took care of our employees and our carriers and our shippers , that this would work out . But we had no clue . When we went and met with Wintrust to talk about a line of credit , I had no idea what the hell we were talking about .
We learned on the go and every day we showed up having no idea what shit we were going to run into , but we just said we got to do it , just do it . Just show up and start and see what happens . Now my parents did not support the idea of me starting this company .
They did not , and my father is someone I've looked up to like a superhero my entire life . I've never thought he could be wrong .
You know , when I was 25 years old , I was 27 years old when I went to him and we were walking the dogs and I said , hey , I want to start a brokerage , this is what I think we can do , and he said I don't think you should do that . He's like I don't think it's a good idea . And I don't blame him . I was a mess when we started the company .
I was a mess personally . I was partying , I was drinking , smoking , gambling . I was doing all this stuff . I was barely taking care of myself .
It wasn't that my father didn't support me , or I don't know if he believed in me then I think he always believed in me but just knew I was dealing with shit , and I think he really was just worried about my ability . If I could barely take care of myself , how could I be responsible for other people ?
So it's hard when people don't necessarily believe in you . Day one , when people aren't saying yes , I think it's a good idea . When people are telling you , I think it's a bad idea . My dad said I think the industry is going to consolidate . I think there's going to be like five brokers left . I don't think you should do this .
That's when you have to believe in yourself . When people are telling you no is when you have to just do it . It's when you have to believe in yourself and you have to . Nobody will do it for you . Whatever challenge you're thinking about doing in your life , whatever itch you have , that's yearning to be scratched .
Whether it's starting a business , losing 10 pounds , putting on muscle , getting a girlfriend or a boyfriend going onto the apps to do so , putting yourself out there . Whatever level of vulnerability you're contemplating , putting yourself through , that's when the fight inside your brain is really important , because the villain is just going to beat you down .
It's just going to keep telling you there's no way you can run a business , andrew Molo absolute no-lo , no-go . Molo is what it says . It says you don't have it and if you let that thing win , you'll never get anywhere .
So , as I think about my life , as I think about various stages of my life , if I hadn't been willing to just do it and to put aside all the doubt and put aside all the feelings of being not good enough , I wouldn't be where I am today . Molo never would have happened .
And when I think about that , it gives me an incredible amount of courage , an incredible amount of belief and confidence in myself . I'm dealing with something similar now in my life with respect to my health . So I'm a tall guy , I'm 6'3" . People who I haven't met always are like I'm surprised , you're LinkedIn .
I would have thought you were shorter , but I've also been a big guy for most of my life . I would have thought you were shorter , but I'm also . I've also been a big guy for most of my life . Um , I like sports , played sports throughout my life , love sports , actually played football , basketball , baseball , but I hated lifting weights , hated it .
I am maybe the most competitive person you'll ever meet in your life . I say that unironically or ironically , however you want to think about it , but I'm not good at seeing long-term . So I love football . I was a linebacker . I love tackling people , hitting people , but I had no muscle .
I was just like a big , lanky dude and had some fat on me , some beef , but no muscle . And I remember going from junior to senior year of high school I was probably going to be a captain on the team . I was a small school , terrible football program with 90 kids in a class . We were not good .
So I was like one of the better of the worst , if that's how you want to think about it . But I remember we had a test every year that was like the baseline strength test . It was just a bench press . I don't remember how much weight , but from my junior to senior I didn't lift at all .
And so when I came into my senior year I could not do any more reps than I had the year before and my coach pulled me aside . He's like I just am really disappointed in you . You're supposed to be a leader of this team and you've done nothing to better yourself this summer , and I think about that sometimes .
I led the team in tackles that year I had a great year . I was MVP of the team , but I could not lift weights and that is something that has carried with me my entire life . In 2020 , was it 2020 ? Yeah , in late 2020 , I'd gotten pretty big . I wasn't taking care of myself at all outside of work . I was now like 260 pounds .
I saw an old picture of myself from I don't know five years prior four years prior and I thought I looked good , but I looked skinnier , I looked healthier , and just seeing that , I said enough is enough . I need to get my shit together . I need to start taking care of myself , I need to start working out , but I still wouldn't lift weights .
I started walking . I found something that my health app on my phone and I started tracking my steps every day . And I started tracking my steps every day and I focused on that alone .
So I'd wake up at 5 am in River North in Chicago and I'd walk down Grand Street I don't know a couple miles until I got to the lake and then walk up the lake a mile or two and then I'd go back , cut through Old Town and get back to my apartment by like 645 . And I was at about 10,000 steps , I can do 6,000 steps in an hour .
So I started building and month over month I went from 12,000 steps a day to 14,000 steps a day , to 16,000 steps a day , to 18,000 steps a day , to 20,000 steps a day . I got to a peak of 25,000 steps a day , which , if you're doing the math , that's four full hours a day of movement . It took me , I think , 10 months to get there . I lost 40 pounds .
I was as healthy as I had been in a very long time . But I couldn't have done that if I hadn't just started , if I hadn't just said one day I'm just going to do it , I'm going to start with just walking and day by day , you build on it .
Now , despite having lost all the weight , I still didn't have an ounce of muscle on my body , and shortly after we sold the company , I went and got an executive health check with a doctor who told me that I had a bad heart , that I have too much calcium plaque built up in my heart arteries , that essentially I have the amount of calcium .
Everybody develops some calcium plaque in their heart over time . Most people don't have any until they're in their like I think 50s , maybe early 40s , mid 40s , you get a little bit . I had the amount that most 60 year olds have , which put me at like a two percent annual risk of a heart attack .
That's pretty scary shit , and yet for me it wasn't scary enough to to change . It wasn't scary enough to make a serious change . It took another year and a half . It took getting fired . It took having nothing but my personal life to really care about my personal life . And so , finally , four months ago , I hired a trainer . I said you know what ?
It's not enough to just be skinny . I need to get healthy , I need to be fit and I need to put some lean muscle on . And so for the last four months , three days a week , I've gone and met with a trainer 630 in the morning . It's been really hard . I dread it . I was dreading it every single day .
Every morning I would wake up and try to come up with an excuse not to go . At one point I missed four out of six . I think my trainer was about to fire me , and that was when my executive coach helped me shift my perspective and stop dreading it , and she helped me think about enjoying the process .
It and she helped me think about enjoying the process , the idea that what if I fell in love with the strain when you're pushing the weight and you feel the strain ? What if you've just loved that ? And I tried to get myself to think that way , and that was a month ago .
I haven't missed a session since , and now I'm looking forward to getting in there and just pushing the weight .
I'm four months into this , so I don't think I've seen a ton of results yet , but I'm in the freaking fight and , as I think about my life , I want to do good things , I want to be a good person and I want to impact people in a positive way , and I don't do that all the time .
There are times where I see people post stupid shit on LinkedIn and I want to tell them I think it's stupid , and then later I'm like maybe I shouldn't have said that , I didn't need to do that .
But the idea is you're going to screw up , you're going to mess up , you're going to miss workouts , you're going to say something you shouldn't have said to someone . You have to give yourself a little grace . You can't let the villain win the fight . He's going to get some punches in , but you have to stand tall and throw him back .
The good guy , the hero's got to stand tall and throw them back . The good guy , the hero's got to stand tall and throw them back and know that every day is a chance for you to do something good .
Every day is a chance for you to take a step forward in whatever you're working towards , whether it's starting a company that people don't believe in you or it's starting a fitness journey . It all starts with the first step . It all starts with committing and then trying , and when you fail , you don't give up .
You iterate , you change the way you're doing it so that you can show up again in a better way . The last thing I'll touch on here before I finish I have to record an actual episode . I guess I'm going to use this , but I'm recording with Prasad in 10 minutes .
And the last thing I want to say as someone with ADHD and a brain that moves a million miles a minute , I have a really hard time slowing down . I have a really hard time following through on things and getting my brain to stop and just relax .
My coach and my therapist have been pushing meditation on me for years and for some reason , I can't get myself to do it , even for five minutes .
¶ Harnessing the Power of Habit Stacking
We hosted Doug Wagner on the show and he talked about meditation . I mean there are meaningful , positive impacts this can have on our lives on my life for sure . To just take a breath , and I can never get myself to do it . So I've recently learned about the idea of habit stacking .
And habit stacking is where you take a habit , something you're already doing , and you pair it with something you can do . While you're doing that , something maybe you're struggling to get yourself to do , and over time those habits become interchangeable . You know , anytime you do one , you're going to do the other .
So in my workout process that I've finally gotten myself to be like excited about , I usually spend an hour in the gym and then they have a sauna and I go sit in the sauna for 15 minutes . Now that is prime meditation time , you would think , but I struggle to sit there and just like be okay .
So in the last few weeks I've started bringing my headphones in there , putting on a meditation for the first six minutes of the sauna and getting that done .
And in doing that I've now done it like seven out of the last nine days , and for me that's a big win , because before that I probably did seven out of the last nine months , seven days out of the last nine months . So I don't know what I'm really saying here . What I'm trying to get to .
What I'm trying to get to is I'm trying to be vulnerable with all of you about where I am in my life , connect with all of you on that , because I know that people struggle , and I know that people struggle just in how they wake up every day and decide am I going to show up to work as my best version of myself , or am I fucking pissed about something ,
or am I just not going to show up at all ? I have that fight every morning of just getting out of bed and I'm happy that I'm in the fight and I'm seeing the results , even though sometimes the results look like one step forward , two steps back for me to then take three more steps forward .
One step forward , two steps back for me to then take three more steps forward .
Whether it's something like Molo that over six years you know I just started with just show up and go and see what happens , block out all the haters and just believe in yourself , or it's a fitness journey , it doesn't matter , you know , find something that you believe in , that you want to be part of , and just do it . Believe in yourself and just do it .
Don't let the bad guy win . You are the good guy . The bad guy is a figment of your imagination . The good guy is who you really are . So I don't know if I'll ever do this again Just me talking to the microphone . I don't even know if I'm going to release this , but fuck , it feels good to do it and it's a step forward for me .
Six months I've been sitting on this . Finally , this morning , when I put on Insight Timer , which is the meditation app I use , I found this meditation that was called I Am and it said I am one of the most powerful words in the English dictionary when put together . I am capable , I am powerful , I am worthy .
If you say that to yourself every morning , you can conquer the freaking world . Believe in yourself , just do it . You .