Jim Love’s story runs from Chicago’s South Side to Milwaukee, where he graduated from Marquette University with a degree in Corporate Communications.
An in-demand keynote speaker, Jim reframed his lifelong stutter into a superpower—first by accepting it, then by laughing with it, and finally by using it to connect.
"Now, I celebrate it and can share that story more broadly on stages across the country," he said.
Today, Jim is a Director of Global Solutions at TAPFIN by day and a speaker and podcast host by vocation, equally on the road presenting to a global client as he is to a gym full of students.
His early highs (a 300-student keynote) and humbling lows (an audience of five) taught him that impact isn’t measured in headcount; it’s measured in changed lives.
From forklift operator to campus tour guide to corporate leader, he carries forward three controllables—attitude, energy, effort—plus a Jesuit-rooted commitment to make everyone feel important.
In this conversation, Jim shares practical habits for mental health, the art of relationships, and how side passions endure when they set your soul on fire.
You grew up on Chicago’s South Side and now call Milwaukee home. What parts of those communities most shaped how you lead and relate to people?
These communities are quite similar: Working class, loyal people with incredible sports fandom and a work hard / play hard attitude. The south side is extremely close knit and we look out for each other.
That family atmosphere shaped me in the sense that I try to form it with people I meet. Milwaukee’s “small city” and caring vibe has made me more open & able to relate to all walks of life.
From a leadership perspective, both cities bring an abundance of culture and varying backgrounds. I lead knowing that I don’t have all the answers and I surround myself with people who are different than me. These communities mean everything to me!
What was an early “gain confidence” moment and an early “humbling” moment that redirected your path?
My early “gain confidence” moment was after my first keynote talk at the ripe age of 24. I spoke to a group of 300 students and felt like a rockstar after I was done; taking pictures, signing folders, etc. I felt untouchable! I assumed I’d be doing this to sold-out arenas in no time.
…my “humbling moment” was my next talk, where 5 people showed up 😊. It was much needed. I took that as a challenge to work harder, perfect my craft and grow my network. Additionally and most importantly, it taught me that impacting 1 life is the most important thing I can do. Quality is always more critical than quantity in my line of work. This was a necessary experience to drive that point home. Now I’ll speak to 1 or 10,000 people!
You’ve held roles from forklift operator to campus tour guide to global solutions director. What did each teach you that still shows up in your leadership today?
Reflecting on that journey is so much fun for me. At my earliest high school / college job of a forklift operator, I learned the value of teamwork and staying organized in a warehouse environment. The teamwork aspect shows up all the time!
I stand by that being a Marquette tour guide is the best job I will ever have - I learned so much and had a blast. Every tour was different and I controlled the energy. As a leader, I know I can control my attitude, my energy and my effort - I did that every day as a tour guide.
In my 20s, I was in a role created for me at a life insurance company. I was responsible for driving membership and I learned how to cultivate my public speaking craft and how to make autonomous decisions in otherwise uncharted territory. I learned so much from success and failures, those lessons will always be with me. As a leader, it’s critical to stay positive during trying times. That role really drove home my ability to stay positive.
Related: Finding communications jobs in Milwaukee
You’ve talked about being a lifelong stutterer. What has this taught you?
Oh man, where do I start?? It has taught me so many things. Resilience, laughing at myself, battling adversity, etc. For me, the first thing was acceptance. It had to be okay for me to stutter. Once I did that, it became humor (my love language). It was okay to laugh about it and humanize myself.
And then it became a superpower. Like, yes, this is what I do, I’m okay with it. More importantly, it taught me that I’m not defined by this adversity I battle; it’s simply part of my life story. That was so critical for me. Being PART of my life and not the DEFINITION of it. Now, I celebrate it and can share that story more broadly on stages across the country.
Congrats on reaching the milestone of giving 100 keynotes to high school students! Can you explain how you got into this work and how has it evolved for you over the years?
It’s something I am very proud of and certainly never thought I’d achieve! It all started back in 2007 when I was nominated to attend a leadership seminar in Chicago. I was the only student from my school placed into this 3-day seminar about leadership (over a summer weekend, no less).
When I showed up, I saw a keynote speaker (A’ric Jackson) who encouraged me to be myself and go “all in” on the weekend. It changed my life and I’ve never looked back. After that weekend, I started to take leadership more seriously and even started writing down my own thoughts around it. It got to the point that I wanted to share those thoughts but wasn’t sure how to do it.
Enter A’ric - in the spring of 2015, he mentored me on how to speak to motivate. It took nearly 8 months to actually develop this keynote and bring it to a place where I could share it. In the summer of 2015, I finally got a shot at the same leadership seminar I went through in 2007 (the Wisconsin version).
I got up on stage, totally blacked out but had a blast. I remember how alive I felt. After that seminar, students from those schools had their principals reach out to me. From there, I built a website and the rest is history. It’s evolved a great deal; I am now a 10 year veteran and a thought leader in the space. I am intentional about where I speak and the messages I am sending. I also go “off script” way more often and that makes it more fun. Overall, it’s my vocation and my favorite thing to do!
What practical advice do you give students who are navigating visible or invisible obstacles?
The first piece of advice is that they are one of MANY people doing this as well. As cliche as it is, they are not alone. So many people have silent battles. My next advice is harder, but changed everything for me: Admit it. Be open about it. When I did that, I realized it was totally okay and it put me at ease. Not being silent about it helps people realize you’re in it together. If you can find comfort, it’s the way to go.
You’ve moved from sales support to Director, Global Solutions. What were the two or three leverage skills that unlocked each transition?
That was an amazing opportunity for me and I am very grateful for it. The skills I had to leverage were my work ethic, positive attitude and public speaking. I had to work harder than ever before given a new role and playing “catch up” against our competition. Some days were difficult…it was (and still is) important to stay positive and attack each day. Finally, I am required to present our services to clients across the world, so my public speaking skills are in full display whether it’s virtual or in-person. These have all been present for the transition and now into my 3rd year doing this job.
Relationship building is one of your calling cards, and you have a famous quote from a Jesuit mentor in your email signature. Tell me about this philosophy.
This is a great question because it’s table stakes to everything that I do. First; relationships are at the core of any success (mine included). Relationships and people matter the most. Keeping that at the forefront changes everything. Second, my quote from my Jesuit mentor (the late Father John Naus) talks about making everyone feel important.
This is in my work email, personal email and hanging above my living room TV. Seeing “importance”’in everyone is not easy, but its so worth it. Father Naus did it better than anyone and I met him on my 2nd day of college. I’ll never forget it and I always end each keynote with bringing him up and parting his wisdom onto students. That philosophy runs deep for me.
You emphasize self-love and mental health. What daily or weekly practices anchor?
These are my favorite because they are wildly underrated. I start each day with a gratitude challenge - 3 things I’m grateful for right away. That puts my mind at ease and is a reminder that things are A-okay :). At night, I do the same things. 3 things I’m grateful for to end that day. Gratitude becomes habitual when I do these things and it really helps my mental health and appreciation for my talents as I start and end the day. Finally, reflecting my comments above, I stay open and vulnerable. I find strength in all of that when I share my story and people identify with it!
Gratitude: Jim and his wife recently welcomed a new daughter to the family
For a high school senior and a college junior, what are the next three concrete reps they should get to build confidence and credibility?
Three concrete reps:
decide today you’re going to accept yourself and love yourself. Success starts with this deep-seeded confidence
Live a life for others. Go sign up to volunteer and find a way to give back. That always helps.
Put yourself out there and SHOW UP to an event, networking or some level of situation that makes you uncomfortable. Credibility and confidence stem from uncomfortability.
Why did you launch the Hustling Sideways podcast, and what patterns have you noticed among people who turn side passions into durable projects?
Allen Halas & I launched Hustling Sideways in January of 2021. We had a feeling there were fellow side hustlers in our networks and thankfully we found hundreds of them. We’ve done over 100 shows and enjoy all of it. We’ve found a ton of patterns; people who are multi-talented, don’t want to settle, are passionate and somehow find a way to connect their day jobs with their side hustles. Additionally, it’s never really about the money. For most of our guests, the early years of their side hustle didn’t yield a profit. It’s more about pursuing a passion and something that sets their soul on fire. That is how they become durable projects; they are relentless and stand the test of time.
How do you decide when a side project should stay a passion, become a business, or be gracefully sunset?
This is a relatively subjective decision, but for me, it comes down to whether or not you’re willing to put in the time to make it successful. My speaking is my vocation and it will always be my passion. For some folks, they are into it for different needs. Ultimately, there’s no wrong way to approach. Just make sure it makes you happy!
Lightning round: A belief you held five years ago about leadership that you’ve since changed, and what changed it.
Five years ago, I didn’t think a positive mindset was a big determiner of success. I realize now how critical it is. Working through 2020 helped cement that for me as staying positive was truly the only thing that got me through it and helped enable my passions.
One small habit that makes a big difference for your teams.
Gratitude. It always works. Every day, stay grateful.
The best question a mentee has asked you.
What do you want to be proud of in 10 years?
If you had 90 seconds with your 20-year-old self at Marquette, what would you say and what would you ask him?
I’d say relax, breathe, be grateful for what you have here because you’re going to miss it. And truly keep doing YOU.
Anything else to add?
My personal saying is “Do YOU, unapologetically.” It’s as the core of my keynotes for 10 years!
