Confessions of an Entrepreneur: First Edition

There are moments, sometimes long ones, when I doubt myself. Today, I am sleep-deprived, probably dehydrated, and feeling older than I should. Being an entrepreneur can steal your dreams even while you strive to reach them.

I'm not one for self-promotion. Don't get me wrong; I love it when others promote me - I just don't want to seem like I enjoy it too much.

Despite writing countless emails each week, starting this newsletter feels daunting. They say you should do what scares you. Since I’m not about to star in a musical, writing a public newsletter it is.

In this newsletter, I’ll share the ups and downs of my entrepreneurial journey, from selling weed to my wife in college to building Wellput today. I’ll also offer insights and thoughts about the email newsletter advertising industry—a field I'm proud to be part of, even though many marketers are unaware of email advertising, and my friends and family think I'm a spammer.

Sales are on my mind this week. My sales career began in the original Silicon Alley building in downtown New York in the 1990s. Back then, the advertising industry was nearing the end of the Mad Men era, with two-martini lunches still in vogue, both the magazine and at Delmonico's. Personal relationships were everything then, and I believe they still are.

Cold outreach isn’t working for Wellput. The algorithms are too good, making it nearly impossible to deliver cold emails. Even when they do get delivered, very few people read them. We could try auto-dialing, auto-texting, or other aggressive sales methods, but honestly, I can’t stand receiving those, so I won’t do them. Instead, we’re going old-school, writing personalized emails to companies we’ve seen sponsoring newsletters or those we think would benefit from it. If you get one of our emails, please respond. We’re creating something magical at Wellput, and I’m too tired for more self-doubt today.

Sent with love.

Craig Swerdloff