Here’s what this week is about: leadership, taste, and staying power.

First, an end of an era. Doug Winter is retiring from Seismic after more than 15 years. I learned a lot from Doug. He bets on people. He stays human. When Seismic acquired Lessonly, I walked in confident and learned hard lessons about scale, clarity, and alignment. I’m sharing those lessons and explaining why Doug’s approach to leadership still matters.

Second, a conversation with Adam Singer on speaking plainly, reclaiming taste in marketing, and choosing mornings over buzz. We often disagree without betraying each other. Why should lawyers advise and not decide, and how does sobriety build persistence? It is a reminder that average work is easy to produce, easy to approve, and easy to forget.

That’s all for this week. Easy, peasy.

♥️ kyle

On What I Learned About Leadership from Doug Winter

It’s the end of an era, one would say. Doug Winter is officially retiring from Seismic.

I talk a lot about leadership in this journey. And Doug is one of the good ones. 

After more than 15 years building Seismic, Doug is stepping down as CEO and moving into a board/advisor role, with Rob Tarkoff taking the helm. It’s a big moment for the company and for anyone who learned under Doug’s watch. 

As an aside, do I smell a Vista acquisition? Maybe. Do I smell a complete revenue suite from Gaisight + Clari + Salesloft + Seismic? Yes. 

But that’s not the point of this entry. 

Let’s get back to Doug. I guess the next question is, what makes Doug different? 

• He bets on people. A lot of the appreciation posts mention that Doug gives people a chance. I was one of those. He took a risk on me when I stepped into the SVP role. I didn’t have the experience (and he knew that) but he believes potential > experience.
  

• He’s relentlessly human. Doug cares deeply about the people doing the work. It’s not performative. He’ll ask about your family and remember the answer three months later.

Now the personal part.

When Seismic acquired Lessonly, I underestimated how challenging it would be to preserve the culture and alignment within a larger company. I walked in hot after 4.5 years of scaling Lessonly, and the leap from a $30M company to a $250M one (managing 30 people to 80) exposed that I was in way over my head.

I tried to do too much and struggled to align a new team to a new system. Change is hard, and I felt it deeply. It felt like a failure at the time, but it taught me the importance of clarity and empathy during periods of transition. Those lessons shape how I lead today.

A few things I learned the hard way (and wish I’d internalized sooner):

1. What worked at $30M won’t automatically work at $250M. Re-evaluate operating rhythms, not just goals.
   

2. Over-communicate culture and alignment—assume decay unless you actively maintain it.
   

3. Don’t carry everything yourself. Spreading ownership is not abdication; it’s how you scale trust.
   

4. Clarity is a kindness. People can navigate hard change if they understand the “why,” the tradeoffs, and the timeline.

Alright, that’s enough about me, back to Doug.

Leaders are measured by outcomes, but they’re remembered by how they treated people along the way. Doug did both. He built a category-defining company over 15+ years and never forgot about the people. 

That’s rare. If you ever have the chance to work with Doug in the future, do it. I’m grateful I did.

Here’s to you, Doug.

On Adam Singer: Free Speech, Sobriety, and Creative Discipline

I’ve known Adam Singer since the FriendFeed days. If you remember that wall of everything from 2007–2008, you’re my kind of nerd. Adam and I finally sat down for a long conversation, and it went everywhere: speaking your mind online, sobriety as a competitive edge, why “hobby” isn’t a luxury, and how marketers let legal steal the keys to taste.

Episode is publishing this week, but here’s a look in writing, the way I heard it.

The courage to speak plainly

Adam’s take on disagreement is simple: if you equate disagreement with betrayal, something has gone awry. That mindset exists on the left and the right. It also shows up inside companies.

He’s posted his views for years, including during his time at Google. The key is knowing the line and not turning your employer into a soapbox for your favorite cause. Bring a moral compass, not a flamethrower.

Practical rules I’m stealing:

• Before accepting a job, ask how they manage employee voices online.

• Don’t let others pressure you to post about the outrage of the week. Silence is a choice.

• If you choose to be a public voice, be consistent and adult. No pile-ons. No “gotchas.”

• Separate activism from your day job unless you were hired for activism.

The “blandification” of marketing

Adam calls it what it is. We’ve professionalized the fun out of the craft. Too many approvals. Too much compliance muscle. Not enough taste. The work blends together until nobody remembers it.

His reminder: marketers, not legal, must be the final arbiters of taste. If you want remarkable work, someone has to own a point of view and ship with it.

AI makes this more urgent. If your output is safe and average, the machines can do it. What’s left for humans is taste, timing, and ideas that move people.

Durability beats buzz

Both of us are sober. Adam has three years. I just crossed a year. We talked about persistence without chemical scaffolding. His line I can’t shake: Do you want to feel your best at night or when you wake up? Drinking chooses night. Sobriety chooses morning.

Also true: reliance on any substance is leverage against your future. You borrow a little focus or confidence now. You pay it back with interest later.

What sobriety gave us:

• Cleaner mornings and more consistent work.

• Presence with the people who matter.

• The ability to push hard without the crashes.

On hobbies, presence, and starting late

I admitted I don’t really “have a hobby” beyond working out and making this show. Adam pushed back. Working out is a hobby. So is building a podcast. A hobby is anything that involves craft and process, giving you meaning and not quietly harming you.

And starting late is fine. When you begin with a beginner’s mind plus adult experience, the work can be special. If you’re raising kids, that season might be the hobby. Be present for it.

Transcendence or drift

Adam wrote that the modern atheist movement gets something wrong. Strip transcendence out of life and most people don’t get freer. They get untethered. You don’t need to return to organized religion to admit you need something bigger than you.

Find a practice or place that orients you beyond yourself. Nature. Music. Prayer. Craft. Something that interrupts the news cycle and gives your life shape.

Narrative vs. impact

We closed on the American Eagle debate and why marketing loves narratives detached from results. Groupthink is strong. Conferences, playlists of “best practices,” and the same five takes on LinkedIn. The cure is curiosity and segmentation. Not every ad is for you. Not every campaign should please the marketing crowd. The work should move customers and the business.

Five takeaways for your week

1. Own your voice. Consistency and decency beat performative hot takes.

2. Reclaim taste. Legal and compliance advise. Marketing decides.

3. Choose mornings. If you want persistence, stop borrowing from your future self.

4. Redefine hobby. If it has process and meaning, it counts. Start now or start later. Both work.

5. Anchor to something bigger. Build a practice that pulls you out of the outrage loop.

Try this

• Draft a one-page “Posting Principles” for yourself. What you will and won’t do online.

• Kill one approval layer on your next creative project. Replace it with a taste review led by the person with the clearest POV.

• Take a 30-day experiment off alcohol. Track sleep, mood, and output.

• Block 90 minutes this weekend for a “beginner’s hour.” Start anything you’ve been putting off.

• Schedule a weekly hour in nature without headphones. Call it transcendence, or don’t. Just go.

I am grateful for Adam’s honesty and range. You can find more of his writing on Substack under Hot Takes, and he’s very online if you want the uncut version.

If you listen to one thing this week, make it this episode.