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Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.
00:00:00:00 - 00:00:22:28
You've had both businesses. Now you think about it reflecting back. What are the biggest mistakes you've made along the way that you share with other founders? Yeah, every big mistake can I? A lot of it has to go for recruiting and hiring, right? Yeah. And you'll get tons of advice in this throughout the path from lawyers, from other professionals, from other founders.
00:00:23:01 - 00:00:36:26
Recruiting is really hard, and you're able to spot it as someone who's not involved in it day to day because there's so many emotions tied to it. I found a friend came up to me. He said, this employee's not working out. Here's the behavioral patterns. This is what it looks like. This is the drag on the company. You're able to spot it pretty quickly.
00:00:36:27 - 00:00:57:13
If you're in this situation and you hire someone that you believe in or that you need at the moment. It's a tougher situation to get out of. To be fair to you and that person. So one of the bigger issues that we've had, maybe not business impact wise, but gut wrenching lies, right? It hasn't been about the money or the sale or losing a strategic opportunity.
00:00:57:16 - 00:01:16:23
It has to do with the people management. And so I hired a really smart individual that was really close. Resume was off the charts. Put this person in charge of a lot of people that I trusted and worked with for years, and it didn't work out. He wasn't the right fit. Yeah, that is my issue. But remove that person getting someone else and that makes sense.
00:01:16:25 - 00:01:38:15
I just waited too long. Yeah, right. And too long. Now I can sniff it out in, like, six weeks of someone being there right? Too long was like six months. And the drag on six months for a company that's only around for five years before exit. That's a huge deal. Absolutely. Yeah. Greg, that that's really fast compared to what I know about you with it.
00:01:38:16 - 00:01:58:17
Was that six months? Yeah. Six months. Yeah. I prefer to actually wait around for, like, six years before making decisions. Right. Yeah. No, because this is super important. Yet two things I think one is it's so hard because like, the founders are passionate, you obviously are. You care about the people. You want them to be on your journey.
00:01:58:17 - 00:02:17:10
You want to inspire them. They're inspired when they show up and then it doesn't work out. That's such a hard thing to deal with. Yeah, that is not it's not trivial. You know, it really isn't. If if I'm honest about it, I can probably sniff it out in six hours, but it will take me six years to to do something right.
00:02:17:17 - 00:02:37:11
And I think that's a common thing among founders. You just we tend to be so optimistic in our sort of outlook toward the world and toward people. Right. You have to be right that it's hard you get in those situations. Mean, let's let's look at the dynamic of hiring someone and putting them in a place higher than a lot of people that you trust and work with for years.
00:02:37:14 - 00:02:50:17
Right. So say this person is in charge of marketing department. You've worked with these people for years. You trust them even if they have less experience in the world. You put that person in charge. No one from that marketing team is going to come up to you and say, hey, I think this is a bad fit, right? I did a bad job interviewing.
00:02:50:24 - 00:03:06:18
You're too close to this person to understand that it's not going to work out. Yeah, a co-founder will do that. So when I say six months, that's after like, let's change out managers, let's change roles. Let's talk to the clients to see if they have the right expectations. Right. Let's try to talk to our team more to see if they'll divulge.
00:03:06:18 - 00:03:26:12
Yeah, if things are going wrong. But it's always the co-founder that says great. Like it's a drag on the business. We need to look at this clearly and let me support you through getting rid of this person. Right. Because a lot of times it comes down to, you don't want that day to come where you have to let someone go, even if you know it's good for them.
00:03:26:12 - 00:03:49:06
They need to move on to right. They're not gonna be successful there. That's when you look at a 50 plus nights, man. It really is. It's never about the finances and the traditional business stuff. On paper. I think it's always about the people management. Right. Because it's hard to align. But a co-founder with an equal level, equal incentive in the business should be able to step in and say, man, we should have done this three months ago.
00:03:49:06 - 00:04:05:00
Yeah, I'll support you in. Let's do this now, Steve, just just a question. Was this a friend of yours, someone you knew before? Is this was this a friend or someone that you. I went to business school with this individual, so we were friendly. Yeah. And I have a huge trust of people I went to business school with, and,
00:04:05:04 - 00:04:25:18
Yeah, he's doing well. But the role that we had and what we wanted to take charge of just wasn't a good fit. So he to saying, because we're fast and growing. I was excited because he was a trusted ally and we had lots of friends. You know, it's interesting, a lot of the things that I didn't see came out after people that I was closer to found out that he worked for us and didn't work out.
00:04:25:18 - 00:04:42:27
And then they started saying, well, yeah, I can see that. And it's back. Like that happened. And then the employees are like, well, you know. Yeah. And then the employees like, after no one gives you the information, why don't they give us the information? Like because they can, Peter. They like they can't. Right. Because what do you really get?
00:04:42:27 - 00:05:01:11
What are you really saying? Right. Yeah. Steve, you did a really crappy job of interviewing that guy. Yeah, right. Yeah. You really have bad decision making skills. Yeah. Right. Right. So you you may have just killed the company. You were blind. When you go, I'm gonna go grab lunch. I'm good. Right, left, right. And so. So this this rings true entirely.
00:05:01:11 - 00:05:17:20
And the team that we had work with for a while, like I trust wholeheartedly. Right. We're in the trenches with them. The few things happen one, once we let this person go, everyone then came out and maybe over a drink or two, or like a coffee chat to say, like, by the way, every time you left the room, his attitude changed.
00:05:17:20 - 00:05:32:24
Right? Right. Because he had he had. Yeah. So and the other thing is the day of that we had worried about and we had talked to lawyers about and how to do this. Right. And the gut wrenching day my co-founder went up to one of our employees and said, hey, I'm going to give you a couple hundred bucks.
00:05:32:24 - 00:05:47:24
Take everyone to Starbucks right now. Right. And just keep them there for an hour. And this individual knew what was going to happen. It's we wanted a calm moment with the person that we had to tell them on. And they were excited. They grabbed like I thought it'd be like oh we're going to lose a teammate.
00:05:47:25 - 00:06:03:07
Like, right, let's grab the card, everybody. Let's go. We got a two hour break, and when we come back, things are going to be different. And there was an air of like, Thank God they're doing something. And that's what you feel like. Holy crap. I've been putting a team I trust in a bad situation for 3 to 4 months.
00:06:03:09 - 00:06:21:27
Yeah. Yes. My job is to leave them of this. Yeah, yeah. And I mean, it's not always the fault of this person, right? You know, and that's the hardest part that you have to bear as a, as someone that hired him, you know, and you, you actually said another thing that was really interesting. You said because I need them right now.
00:06:21:27 - 00:06:45:29
I need this support right now. We've heard that before where you hire for this moment and you're not planning, and then you're like, well, that moment's now gone and this person's still here now, right? Right. Yeah. Right. You know, a while ago, like I wrote a book this is back a decade ago. And one of the things we talked about in it was what, you know, it was the book is called Hire Fire in the Walking Dead somewhere.
00:06:45:29 - 00:07:12:20
There's probably a copy, something like somewhere that can be. I've got one for you, but but we talk, you know, we talked in the book about this concept of, like, a desperation hire, right? And nine times out of ten, that's where this that's where all of these things come from. It's it's that I needed this person, right? I needed this role filled the worst hires I've ever made, the most catastrophic hires I've ever made have all resulted from that same thing.
00:07:12:23 - 00:07:32:21
Right? I need to fill the role. The person almost becomes secondary. You'd never articulate it like that, but that's what end up. That's what ends up happening. Yeah. Put yourself in the role of the mentor. Advisor for a second. Right to another founder, another founder sitting here earlier in their career than you are. What's the advice you give them about this?
00:07:32:26 - 00:07:51:12
Wow. Yeah. It's, it's advice that my, one of my attorneys gave me early on from Dallas, which is hire slow and fire fast. Right. Use sounding boards, use an attorney, describe a situation and have them tell you. Hey, I've seen this 400 times. This is what you need to do and then bear the emotion.
00:07:51:16 - 00:08:12:21
Hiring slow is one of the key portions of it. So you have to get ahead. You have to predict the stuff, not get in trouble with needing someone right now. And you'll see there are ways to understand if someone's intrinsically motivated, has the skills before you hire them, like they're going to invest all their time with you over the next few years and have options in the company like they're going to be involved.
00:08:12:22 - 00:08:33:10
You won't be able to get them away from projects or trying to give advice or asking for more updates before they're even interviewed or on board. So hiring slow is is easy to say in practicality. You always have to be recruiting because chances are the next hire. Yeah, even if we haven't signaled it or interviewed for it, chances are we already know them because they're close to the company because they're motivated to do so. Yeah.