I’ve known this Founder for over 2 and a half years now. I actually invested in his start-up via a SPV just after their Series A. We do business together, and he’s a smart, great guy. But why I think this is a cool story is because when we met, he really didn’t want to use a “freight-tech” recruiter. Now that I think about it, I don’t think he wanted to hire anybody from freight, either.
Maybe I’m too proud, but I wouldn’t say I was useless to him. He heard “freight-tech recruitment” and had a clear idea of what came with it. He wanted people who were super curious, moved extremely fast, with high agency and fit his culture. In his mind, he didn’t think those people were working in freight.
He wasn’t shy about it either. He told me all of that right to my face. I mean he was kind, but you could tell that he is on a mission to hire the best people in the world, industry be damned.
“KJ, Can I Be Honest?”
We met at BGSA, Ben Gordon’s amazing conference at The Breakers, over 2 years ago. It was at the big cocktail party, and I asked what he thought about the industry because he wasn’t from it.
He looks at me and goes, “KJ, can I be honest?”
I go, “Please.”
He said, “I don’t know that anyone in the freight industry is curious enough. I don’t know if they can move quickly enough nor operate with enough agency. And I just don’t think they fit the culture I’m trying to build.”
Truth be told, I liked his answer. He didn’t give me the polite version and disappear. He told me what he thought, then asked, “So, with that said, what do you think I should do?”
I told him, “Well, then perhaps you may want to look at adjacencies. Have you started hiring from Samsara, yet?”
He said, “That’s kind of where we’re looking.”
The Big Logo Isn’t the Whole Answer
I understood his logic. Samsara had technology people who understood physical operations. The only challenge, in my mind, was that the company was way past its IPO and everyone working there has a lot of resources that you just don’t get in a start-up.
I told him it could work out really well for him, or turn into the same thing we see when people in freight hire from C.H. Robinson. They see a great person with a great company on their résumé and assume all of it travels. Sometimes it does. But sometimes it doesn’t. Often, that person gets to a startup, looks around for the 4 departments that used to support them, and realizes those departments are now one person. You.
You’d better know which part of their success belonged to them and which part belonged to the machine around them.
So they tried the Samsara route. It didn’t quite work out.
Then He Saw Me With the People I Knew
Later, my good friend, Travis Rhyan, was hosting a party at Manifest. I’ve known Travis for 15 years, and I was sponsoring his event. This Founder wanted to come, but we were past capacity for the space we rented. He didn’t give up. He called my buddy Dalton Tielens, he texted Travis, and of course he found a way in.
And then once he walked in, he saw me in my element, in a room where I knew everybody.
Andrew Leto was there, I used to report to him. Kevin Nolan from NTG was there. Person after person kept coming up to me, dapping me up or giving me hugs, because I’d worked for them, recruited for them, and knew most of them for years. Something you don’t get from a simple LinkedIn connection.
The founder watched all of this, then came over to me. He goes, “You really know, like, everybody in the industry, don’t you?”
I said, “Most of the ones that matter.”
That was what he had been missing. When I said “freight tech,” he heard a limitation. In that room, he saw the network. I knew who had built something, who could move quickly, and who needed a big machine around them. I also knew people coming into freight from other parts of technology and really from around the world.
Then, just like that, he asked me if I have ever invested in start-ups in the space.
I replied, “Absolutely. I think that would be amazing.” So I invested.
Six or 8 Months Later
Six or 8 months later, he finally came back to me and said, “I think I do need a few people from the industry.”
He’d tried what he thought would work and learned something. I respected that he came back and said it. Plenty of people will drag a bad assumption around for another year because admitting it was wrong feels worse than paying for it
His startup still needed the curiosity, speed, high agency and culture he cared deeply about. It also needed people who understood the customers and the industry it was selling into.
We looked in both places. We placed people from Palantir at his company and brought in freight-tech experience, too.
Founders sometimes decide the résumé before they’ve decided exactly what the person has to do. Six months later, they’ve had plenty of conversations and haven’t made a hire, and somebody finally asks whether the original sandbox was the problem.
Often, It Goes the Other Way
What happened at this startup was almost the reverse of what I’d seen at project44.
I’ve known their Founder, Jett McCandless, since 2007. He sat in the cubicle next to me at GlobalTranz having started two weeks before I had. We always stayed in touch and have even gone heli-skiing and raced Baja trucks in California.
When Jett started project44, he did what everybody does when they start a freight tech company. He hired people from freight.
Then project44 got to around $10 million in ARR, and he said, “I think I now need Enterprise SaaS talent.” Later, it became, “I need the best technology sellers and the best technology operators in the world.”
You start with the industry, then you get to scale and realize you need talent from outside it. The startup in this story started outside and came back for some industry talent. We placed Palantir people at both companies.
That’s why the industry label never told the full story. I knew the freight people. I also knew how to find the Palantir people.
What Changed at 10 Point Partners
My own business had gone through the same evolution. I spent 2 years inside project44. We built a 34-person talent acquisition team and made 1,053 hires around the world in 12 months. My first job was finding somebody to get us into China. I had never done that before. We figured it out.
The second year, I worked on replacing every executive at the company except for Jett and the President as the company got IPO-ready. I performed some of the searches and hired retained firms for others. This gave me the opportunity to study executive search from the client side.
When I came back to my firm, I knew I wasn’t going to continue building a contingency firm around freight brokerages. I wanted to keep pushing through freight tech and into enterprise SaaS, AI, Robotics and even Defense Tech. I ripped the business down to just 3 of us and rebuilt it.
So when a founder hears “freight recruiter” and decides I can’t reach the people they want, I understand how they got there. I also know it may be costing them 6 to 8 months.
Tell me about the role. Tell me who you think you need and why. If I agree, I’ll tell you. If I think you’re looking in the wrong place, I’ll tell you that, too. Then we can get to work before another 8 months slips away.