Today we’d like to introduce you to Nathan Hall.
Hi Nathan, thanks for joining us today. We’d love for you to start by introducing yourself.
My story does not start with a business plan. It starts in a whole lot of hospital rooms.
I want it on the record that I am not some naturally brave guy. Most days I am an adolescent hot mess who learned to crack jokes in scary rooms because the alternative was falling apart. Humor was never a personality for me, it was the survival plan. I have a rare artery disease, a couple chronic illnesses, and more surgeries than I can keep count of, and somewhere in all that waiting room time I got weirdly good at the one thing I am actually built for. Being okay when everything is not okay, and helping the person next to me get there too.
Then we had Zoie. My daughter was born with hypoplastic lefty heart syndrome. First open-heart surgery at 31 days old, three more before most kids lose a tooth. And here is what nobody warns you about. The hardest part was never my own body. It was watching my wife Mickey and my kids Zane and Zali hurt right alongside all of it. When you love people, your pain becomes theirs, and there is no surgery for that one. Zoie taught our whole family how to be brave on the days none of us felt we could be. She is still the toughest most inspiring person I have ever met.
Somewhere in the middle of all that I quit being scared of hard things and started walking toward the scared people instead. I could not help it. I have never once been able to walk past somebody having their worst day.
Here is the other half of it, the part that actually built Lefty. I never fit the box. Every regular job I ever had, this brain of mine, the one that cannot stop asking why and sees patterns everywhere and can read a room and people right when I walk in, kept getting me treated like I was difficult. I was not difficult. I am just weird without trying to be weird, and most workplaces are not built for weird. That is honestly nobody’s fault. Most people fit the system fine and do great inside it. I was just never going to be one of them, and pretending otherwise was quietly suffocating me.
And there was a bigger thing that box could never hold. Our family cannot live by business before family. When your kid has a heart that needs surgeons, family is not the thing you squeeze in around work, it is the whole center of gravity. No boss’s expectation was ever going to come before a hospital bed, and it never will. So I stopped trying to bend our life to fit a job and started building a job that fits our life.
That is really why Lefty exists. So our days get built around the people we love instead of somebody else’s number on a whiteboard. And here is the part I get almost annoying about, I want that for everybody else too. I want the baker and the coffee shop owner and the guy running his whole operation out of his garage to get their time back and their family back, not hand their one life over to the grind.
So when AI showed up and I watched regular business owners get that exact wide-eyed, stomach-drop look I had seen a thousand times in a thousand rooms, it all clicked into one thing. Here was a way to help people get found, keep their doors open, and still make it home for dinner. Nobody was sitting down next to them offering that. So we did. Lefty did not get born off a spreadsheet. It got born out of a waiting room, out of a family that had to do life differently, and out of a stubborn guy who refuses to believe you have to choose between a living and a life.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Smooth road? I have not seen pavement in years. Mine has been gravel, potholes, and a couple of bridges that were not even there with no sign or warning.
Here is me being what life and my amazing parents taught me to be, honest and humble. The hardest part of this work is staying honest inside it. When we sit down and tell a business owner the truth, that nobody can guarantee a number, that this is barely two years old, that anything worth having takes time, some of them want a quicker, shinier answer than we are willing to give. So the truth costs us deals, and some months it costs us money we genuinely need. We pay it anyway, every single time, because the moment we bend on that we stop being us.
Honestly though, the hardest part and the most fun are the same exact thing, teaching a market that does not exist yet. Half the people we sit down with are still thinking SEO, backlinks, keywords, conversion rates, all these words that were built for Google and just do not translate to a world where somebody asks a machine a question and gets one answer back. There is no page two in an AI answer. So a huge piece of the job is helping people unlearn the old rules before we can even start teaching them the new ones. It is exhausting and it is my favorite part of the week, usually in the very same meeting.
And we feel a genuine responsibility in it, which is exactly why we are fighting to get here first. Not to plant a flag, but because whoever shows up early sets the tone for everybody who comes after. We want to be the ones who got here honest, who set honest expectations and made a scary new thing feel like something you can actually trust a person with. Somebody has to be the calm hand on this one. We would like it to be us.
And I will be straight with you, we are not running this off some cushy runway. Broke some months, tired most of them, putting one foot in front of the other because we believe in it more than we are scared of it. Life has never handed my family an easy stretch, so this is just the version of hard we actually got to pick. That part honestly feels like a gift.
The biggest challenge was never the work. It is not letting a bad day talk you into cutting a corner or telling a pretty little lie. We have not, and we will not. That is the whole company in one sentence.
Appreciate you sharing that. What else should we know about what you do?
We are a collective of whys. Best way I know how to put it. Get us in a room and one dumb little question turns into a three hour rabbit hole nobody planned, and that is usually right where our most creative ideas are born and somehow work.
The work is AI discoverability. Somebody stops Googling and just asks ChatGPT, Claude or Perplexity for the best coffee shop or baker in town, and most small businesses are nowhere in that answer. Gone. Invisible, and nobody ever told them. We find them and pull them back into the conversation.
The fun part is how we get there. We built our own AI and named her Nova, and then we kind of got carried away, because now there is a whole cast of them with opinions. Nova runs the data and roasts me for sport. Goose builds and argues with everything we say. Vox is the one who actually sounds human. And here is the part I find genuinely fascinating, they take sides. You will watch an AI start playing favorites with one of us over another, and then the humans turn around and do the same thing right back. It is never just AI against me. On any given morning it is anybody on anybody, machines and people picking teams, and somehow the truth falls out of the middle of all of it.
Because that is the whole thing. The truth. AI runs 24 hours a day and never sleeps, but the piece that actually matters, the one that is never going anywhere, is a human who cannot stop asking why. We call them Guides. A Guide is the one who looks at a score that came back gorgeous and says nope, too good to be true, because they know the client, they know the client’s whole world and market, and they can feel it when a number is lying. And we do not stop until we can hand somebody the truth, whatever that truth turns out to be.
We are also just honest about what this even is yet. This whole AI search thing is barely two years old, which means two years of data is all that exists in the entire world, us included. So we will not promise you a score or a percentage, because nobody can promise that honestly yet. What we can promise is the work. The numbers are born out of the work, never the other way around.
And the real reason we lean on AI this hard is not the AI. It is what it hands back. We use it to give people their time. Their Fridays. The afternoon somebody gets to be a mom or a dad or a grandparent instead of buried in a dashboard. If a machine can handle the around-the-clock part so a human gets to go home, that is the entire point.
That is Lefty. A pile of too-curious people, a few mouthy machines, and a stubborn refusal to hand anybody anything but the truth.
Before we go, is there anything else you can share with us?
If there is anything left to say it is just thank you, with a little bit of pinch-me mixed in.
I have to talk about Kareem Rush, well because he was my most favorite MU player ever. Kareem is my partner and runs our business development, and he is genuinely the most thoughtful, most honest person I have ever met. We have been a better team since the day he came aboard, and I do not mean that in some vague nice way. He is the reason we do the right business and get the right business, the reason we end up working with people who actually fit what we believe in. I want people to know his heart not just his success in basketball.
Thank you to the crew that roast me 24/7, Mickey, Lachelley, Kevin Stucker and Leo. The people who roast you hardest are usually the ones who love you most, and I am buried in love. I am very blessed to have them along for the ride.
Thank you to my family. I am blessed with such amazing parents, Dub and Jan Hall, brother and sister in law Chad and Stacy Hall and my family Mickey, my beautiful wife, and my kids Zane, Zoie, and Zali. Everything I build is just an attempt to be worth the patience they have shown me. They are the whole reason any of this exists, and the whole reason I want other people to get their time back too.
It has been a wild little stretch, and I am honestly still not used to any of it. We are all over 1 Million Cups here in Kansas City, and I get to present at 1 Million Cups up in St Joseph soon. We got picked as one of only 20 companies in the whole city to get a table at the Kansas City AI Expo, which I am half convinced is a clerical error. We recently got to sit down on the Beyond the Build podcast and will be on more here very soon. A guy who grew up in a lot of hospital rooms, ending up at tables like these. I do not take a single second of it for granted.
Mostly I just want to be the calm honest one in a scary new corner of the world. That has been the assignment since the very first waiting room, and it still is.
Contact Info:
- Website: https://leftymediaco.com
- Facebook: https://www.facebook.com/leftymediaco
- LinkedIn: https://www.linkedin.com/company/leftymediaco
- Other: https://leftymediaco.substack.com
