Executive Insights featuring Kate Bradley Chernis, Founder & CEO, Lately.ai

I’ll admit it, I fangirl hard for Kate Bradley Chernis. She’s cool.

At the end of my interview with her, on a whim, I asked the former SiriusXM DJ to compile a playlist for me. My jaw was hanging when she was finished. No Elvis Costello or Ricky Lee Jones for me. Instead she chose the Jayhawks, XTC, and “that dirty song” by Lucinda Williams. It was live Spotify. Her brain functions like an algorithm and sees patterns between the rhythms of music and language, connections between the tip of one song and the tail of the next.

But I was fan-girling for her before she created my very own personal playlist.

Since meeting Kate in New York eight years ago, I’ve come to appreciate many things about her. She is warm (we both say I love you when we sign off Zoom), her LinkedIn posts are strewn with emojis, vernacular and opinion.

Can I swear on your show? she asks.

She offers a master class in writing for sales and marketing. She writes like she talks (and recommends this), using a voice-to-text app.

When I left the corporate world and decided to go solo, she was one of the first people I asked for advice. She recommended the book her husband gave her when she started her own business: The Art of the Start. ‘Don’t wait. Just jump in,’ she said, summarizing Kawasaki’s bestseller in five words.

Compiling a list of the entrepreneurs and founders I wanted to interview, she was at the top. Because she is the badass lady boss, founder and CEO of her own company, Lately.ai, and a relentless innovator of AI-driven content for marketers.

In less than an hour she references cultural touchpoint and banjo maestro Bela Fleck, podcaster and philosopher Sam Harris, and social guru Gary Vaynerchuk (an advisor to Lately). If you’re a social media manager or director and you’re not using Lately, close your shop and go home because you’re wasting your time. This is your boomer mom talking, kids. It chops and chunks any long form content and spits out snackable video, audio or text for your social media channels. It’s the only A.I. platform that creates social media content.

And now it’s integrated to Hubspot and Hootsuite.

I use the product and love it.

Raised in upstate New York by entrepreneurial parents, Kate still lives there.

She can reel off a playlist thanks to her days as a DJ in Vermont with hippies where she “learned so much.” (Once, on April Fool’s Day, they played Sheryl Crow’s All I Wanna Do is Have Some Fun on repeat all day.  “People were calling in,” she says, laughing). From that she went to running marketing campaigns for Walmart where she achieved 130% ROI for them year on year, for three years with her signature brand of digital marketing, to CEO at Lately, her digital media startup.

I had too much to say about Kate to run this as a Q&A. If you want to hear her verbatim, listen to one of the many podcasts she has been featured on. My goal was to imagine her on the cover of Vanity Fair (google her, it’s not a stretch) with this story on the inside (an actual stretch).

Before I even hit record, we had gone down a dark hole discussing drinking and exploring our fraught relationships with alcohol. In fact, I was going to open this piece by saying something like Kate is the kind of person I want to do tequila shots with. Thinking how cool that would be. Well it’s not.

“The vulnerability, all our ailments – not sleeping, digestive, dry hair and skin, bloating – all go back to that second glass of wine,” she says.

She explained that she had stopped drinking during the week. It reminded me how a friend once posted on Facebook that she was only going to enjoy what Kate calls “Mommy juice” on Friday and Saturday nights. What a revolutionary idea, I thought. I’m married to someone who abstains but also live in a society where a glass or two of wine with a meal is perfectly normal.

Kate recommended Quit Like a Woman and I devoured everything I could find about the book and author, Holly Whitacker, immediately.

Here are some outtakes from our conversation, edited for length and clarity: (Full disclosure: this interview was conducted in January 2022 and is only published now due to my own lack of discipline).

AD: Is it true that the team comes to you once a year and sits around on your floor and eats tacos and goes skeet shooting and bonds?

KBC: It’s true. The best way to create a culture is to break bread, right? I like tacos the best. It forces you to reach over. It’s messy. And there’s always a job for everyone to do as well. You want to make sure everyone has a task. We bring our air mattresses. There’s no work. We just hang out, have some fun. I love having them here and I have an arcade, so it’s cool to be here.

How hard has it been for you to get funding as an entrepreneur?  

A lot of people like to tell you, you can’t do it. 

I actually call people out on it. Once I was trying to close a venture capital deal and part of it waned on their marketing team using the product and enjoying it. And the marketing person was a consultant. I knew right away that was gonna be a challenge. I also knew that when they tell you to use something, people always hate that. She killed the deal in a way that she didn’t even have to. I called her afterwards. I said to her, just to be really clear. I only get 2% of all the venture funding. I have to work 98% harder than white guys. And you aren’t helping me. It’s okay to not help me, but you hurt me. 

You’re up against a lot of barriers. You’ve got a start-up in New York City with a digital marketing product that kicks ass and that everyone loves. I’m surprised investors are not knocking down your door. What do you have to do to get that? 

I was just on a call with one of my favorite mentors and investors. You learn who to call at the right times. I’m very, very grateful. I pull in different people at different times. So this particular person always can cut through the noise and give me really clear advice for fundraising, but then also my mindset, and he said to me multiple times, he said, this is a really good story and the way you’re framing it is super pessimistic.

And he’s right. I mean, my special gift is seeing the glass half empty. We joke about that at Lately. I mean, that’s what makes me a good CEO is I’m always looking for the problems so I can fix them.

So is it a question of rewriting your pitch or working on the positioning or what was his advice?

It’s really like, it’s already right in front of you. And he’s looking at me like ding-a-ling, you’re doing all the right things. Just get out of your own way.

What’s next for Lately?

I had a mind shift last summer. I always know when I need one. I’m really good at pulling people or events in my life to change the channel. I did that this (past) summer and it’s funny when you open the door and you’re willing to do that, then the right change makers come your way. I was really lucky because Mark Roberge happened to be that change maker for me and Mark, just for those who might not know, is the former CRO of HubSpot who helped get them to IPO. 

Another friend and investor asked me, are you happy? And the answer was no. Around Lately, the things that make me happy are working on the product with my Chief Product Officer Jason. I love product design, UI and UX and writing.

So it was the combination of Mark and me knowing this is what I wanted to do. Also having a real reassessment of what my founder skills are and our skills as a team. I had this huge aha moment. I was like, wait a second. The Universe is trying to tell me this. Jason, for example, he single-handedly built small, medium business tools for Target and Bank of America. So his specialty is designing products for the “every person.” My specialty is broadcasting to 20 million listeners a day for XM. And converting B to C for Walmart 130% year over year, over three years. My job is talking to consumers. That’s what I’m really good at. The “every person.” So, light bulb. What we had set out to do with Lately was address this audience. The idea was, what I’m doing for Walmart, they’re paying me $140,000 a year. Let’s give you, Angela, the same ability to do it for like five bucks a month. That’s what we set out to do eight years ago. And then we got away from it, we got distracted.

Last summer, we started looking at the data in a new way. This is where Mark came in. One of the best tips I ever heard from a fellow entrepreneur, James Lee, was to look for the patterns, because you either want to double down on them or fix them. Now I could see patterns within the patterns, which pointed to something that was in my gut that I’ve been saying for a long time, but I didn’t have the data. And that was to flip the product upside down, pull us out of publishing altogether, create focus on self-service and focus on product like growth. Mark’s specialty.

So we’re focusing now on the AI, which is what we do best. We don’t want to be a social media platform. There’s people who do that already. Why am I remaking the wheel? This sounds so obvious, but it’s not when you’re in it. And how can we focus on what we do best. You can automate content creation. So that’s what we’ve done and we can sequence it. We can gamify it. We can make it fun. We can make it less overwhelming. I have an AI team specifically focused on enhancing the capabilities of the content creation.

Bonus for getting this far – I noticed on Kate’s LInkedIn banner a photo of herself with the Rolling Stones. I asked her, the former DJ, to create a playlist off the top of her head for me. Here’s my playlist:

  • Queen of the World, The Jayhawks
  • One Headlight, The Wallflowers
  • Essence, Lucinda Williams
  • Earn Enough for Us, XTC
  • I Am A Leaver, The Damnwells

Thank you Kate!

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