The Business Bag: A Mailbag With Business In The Title

The Business Bag: A Mailbag Under The Guise Of Business

Welcome to the first ever business bag, which (I guess) is just a mailbag for business. Actually, I don’t even care if they’re business questions. I just wanted to do a mailbag because it looked like fun, and I don’t always get a chance to answer your questions on the podcasts. I’ll answer just about anything. If it’s a good question, you’ll probably see it in the business bag. Shoot me an email, and if it’s unique, I’ll do my best to answer it on here.

I’m looking for tips on how to close my first seed investment round.

Sent from my iPhone

First, thanks for the question, Slayter. Closing your first seed investment round is a major milestone for any young entrepreneur. I like to think of round 1 in terms of street fighting. Play by the rules, for now. Round 1 is normally more of a feeling out process for all parties involved. Don’t overextend yourself. One wrong move and you could end up on the concrete with a serious head laceration. Not a great start to your business, in my opinion.

Based on what I know about you from you email, your name is Slayter. That’s a dope name. Everyone automatically thinks of A.C., but when it comes to Slayters, or Slaters, consider me a Slater from Dazed and Confused guy. He was chill and rolled with multiple crews. They don’t make them like that anymore.

I’m assuming you’re starting a business for the prestige. Tossing a few Facebook posts up to create some buzz, then hitting send on that mass request for people to like your page. That’s what this is all about. You’ll never forget the early days. Keep that in mind when seeking angel investors, and be weary of whose money you accept because you’re going to be dealing with these people often. Happy hours and SXSW parties? They’ll be there with t-shirts under blazers, because that’s what angel investors wear. Once you lease a little office space, they’ll drop by unexpectedly just to tag themselves in a pic so all their friends know they’ve diversified their portfolio. You’ll be seeing a lot of them, so choose wisely.

My refusal to buy middle-of-the-mall loafers means I have to select between my bit loafers and penny loafers. Unfortunately, I’ve learned that not every loafer fits every situation and showing up wearing bits to client meetings might come off as cocky. Do I need to sacrifice quality and diversify my shoe collection, or should I own my looks in the boardroom even if they rub people the wrong way?


Great question, Tad. I get this one a lot, and honestly, there is no “right” answer. Bit loafers are polarizing; there’s no denying that. But, if worn correctly and confidently, you can easily go from “Dallas douche with the loud chain shoes” to “sharp guy from the big town who knows his shit.”

When entering a boardroom, you should aspire to be a blend of modern day Mariah Carey and Clint Eastwood at the 2012 Republican National Convention. Modern day Mariah still possesses all of the tools needed to be working with high diva status, but she’s living on a rep she built in the nineties. Nice. Everything was better in the nineties. Now Clint on the other hand? Clint built his brand on being the strong, silent type. That’s why we were all blown away when he spoke at the RNC and just lit the crowd on fire with a zippo lighter and a bottle of hair spray. Total wildcard.

If I’m putting together a dream team board, I want people who can give me both. Variety is the spice of life. Mix it up one time for me, please. If you keep them guessing, they’ll never be able to pigeon hole you.

What’s the biggest misconception about closing that you see? I’m very successful, and I see my subordinates making the same mistakes over and over. I’m interested to see your thoughts.


Congrats on the success, Jack. One mistake I see over and over is overthinking. If you ever have to think to yourself, “Okay, time to close,” you’re out of the flow. The deal is no longer organic. Something happened during key moments to push the ship off course. That’s fine, but it won’t feel the same. Those are called fleshlight deals. You end up in the same place, but it’s not the same.

You can still make it happen, but you’re really running the risk of being in your own head. Once you’re up there, you’re unknowingly inviting others in there. Before you know it, you’ve got a kitchen full of wolves waiting for you to make a mistake. Let it happen naturally, and you won’t be eaten alive by wolves in your kitchen.

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Lawyer. Writer. Dude doing business. I'm the meatloaf guy from tv.

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