Tag Archives: Podcasts

My Fourth Appearance on AI and The Future of Work

This is a quick post to announce my latest appearance on Dan Turchin’s AI and The Future of Work podcast.

Dan, the founder/CEO of PeopleReign, has been doing AI since long before it was cool and, to give you an idea of how long he’s been podcasting about AI and the future of work, my appearance marks episode 324 of his podcast. He’s no Johnny-come-lately to the fascinating intersection of people and technology and his material is always worth a good listen.

In what’s become a tradition, I’m back on the show to talk about my 2025 predictions blog post. In the 43-minute episode we bounce around a lot, but cover these topics:

  • The evolution of search: answers, not links
  • LLM optimization, how to show up in LLM-generated answers
  • Why it’s dangerous to think you’re lost in a “sea of sameness” when it comes to product differentiation
  • Why branding isn’t the last bastion of differentiation
  • Why to track Rand Fishkin when it comes to the evolution of SEO to LLMO
  • Why general-purpose databases are generally good at absorbing special-purpose databases — but not always
  • Does Europe’s tendency to greater regulate have any hidden benefits?
  • The Robin Williams quote about Canada: “it’s like living in the apartment above a meth lab.”
  • How America-first VCs will likely shoot their feet off with European companies and entrepreneurs
  • Why I predicted that LinkedIn will likely follow the path to enshittification by following engagement as their north star

I’ll conclude by saying that the Future of Work has become one of my favorite topics. It started with my Clubhouse room (remember Clubhouse?) with Thomas Otter. That led to some ongoing collaboration with Thomas when he moved to become a partner at Acadian Ventures (which, by the way, is an investor in PeopleReign). That also eventually led, through introductions to the founders, to my joining the board of TechWolf, where I’m now learning about redesigning work, people-centric data platforms, and the skills-based organization. It’s a fascinating area, particularly here at the dawn of mainstream AI, and one that affects all of us.

Thanks again Dan for having me on the show and for a great conversation about the predictions and a whole lot more.

Appearance on ProducTea with Leah Tharin

Just a quick post to highlight a recent podcast appearance with Leah Tharin on ProducTea, a European podcast focused on bringing together product, revenue, and growth. In addition to her podcasts and blog content, Leah produces a number of guides that are quite useful for startups as well.

In this, my second appearance on ProducTea (my first one is here), Leah and I have a pretty wide ranging discussion. Topics include:

  • Understanding the Dual Role of a CMO
  • The Ownership of Growth: A Collective Responsibility
  • Organizational Design: Indicators of Health and Conflict
  • The Complexity of Metrics and Data Overload
  • Cross-Functional Collaboration: The Role of C-Level Executives
  • The Importance of Internal Curiosity
  • Lessons from the GE Hawthorne Experiments
  • Feedback and Communication in Organizations
  • Five Principles of Organizational Design
  • Designing for Healthy Conflicts
  • Rethinking Marketing Qualified Leads (MQLs)
  • The Role of Incentives in Organizational Success
  • Establishing Fail-Safe Processes
  • Challenges Faced by Smaller Companies
  • The Need for Humility in Startups
  • The Complexity of Large-Scale Projects
  • Understanding Time vs. Money in Enterprise Sales
  • Practical Advice for Implementing Change
  • Managing Big Projects Effectively
  • Staying Alive in the Competitive Landscape

The episode is available on Spotify, Apple, and YouTube, with the video embedded below.

Who, Me? The Brand Curmudgeon? Appearance on the Standout Startup Brands Podcast

I was thrilled to get together with Janessa Lantz (former CMO at dbt Labs) to join her and Amrita Gurney’s podcast, Standout Startup Brands, to discuss a topic that most people don’t even want to talk to me about — branding!

Yes, I’m known as something of a brand curmudgeon, but I’m also very much a marketer and I do care a lot about branding — but approach it with pragmatism, caution, and healthy skepticism.

Here are some of the highlights from the episode:

  • To me, branding is about trust. My definition is quite meta, but it’s trusing that you will be you. Trusting that you look like you. That you sound like you. That you act like you. That your execution is consistent with your vision. Basically, have you defined a clear character and are you staying within it? You be you.
  • It starts with hygiene factors: is your corporate image even professional? Is your copy error-free and mechanically consistent (e.g., via style guide). They’re called hygiene factors because you get punished if you land beneath the bar, but get no extra credit for being above. For example, you might not hire someone who arrives in very dirty clothes, but I doubt you’ll pick the top candidate based because they wore the cleanest. So any money invested in coming in above the bar is effectively wasted. Clear the bar, but by an inch.
  • Consistent messaging across deliverables is arguably a hygiene factor. I wouldn’t think your terribly professional if I heard a different story across SDRs, sales, the website, a live webinar, and in reviews from industry analysts. Consistency is key to communications effectiveness, but it’s also a hygiene factor. Some people notice. The smart ones, I think.
  • You can stay consistent by making a marketing blueprint deck, a deck that captures the answers basic questions (what is it, what are the benefits of using it, why is it different, etc.) in a master deck that you continually update and reference as you build marketing deliverables.
  • Consistency is hard with genius founders who often have too many great ideas. To manage this, you need to get their buy-in about their best delivery and then standardize on it. And then hold accountable for not changing it every day.
  • If there’s a technical story behind your product, you should make a seminal white paper that tells it in about 8-12 pages. You’ll be surprised how hard this is — particularly with platform software — and it will help you both tighten your story and tell it consistently. It’s literally the first thing you should at a zero-to-one startup on the marketing front. (Writing it will also help you get started on the style guide.)
  • Why do I say “wait until you’re $100M until you focus on brand?” or “if you want to build a brand, go sell some software?” Because capital-B branding — hiring an agency that has no intent on tightening product message or increasing pipeline, but instead helps you determine brand values, brand promise, brand platform, etc. — usually can wait. Some marketers want to do it too early. Heck, it’s fun. But don’t do it too early. Simply put, if you’re $15M and not growing, nobody actually cares what you stand for. So don’t spend $300K trying to figure it out. Get big enough to be relevant, then tighten up who you think you are.
  • Most $100M companies still don’t have tight product and corporate messaging. Get your priorities right. Fill the pipeline. Helps sales win deals with product, competitive, and corporate messaging. And when all that is working (and if you’re hearing about troubles due to a lack of branding) then go hire an agency to work on capital-B branding. And I am not universally opposed to this! For example, I recently had a great experience with Twenty-First Century Brand on a branding project. My argument isn’t never. It’s be sure you’re doing it at the right time and place in your evolution.
  • Building a strong leadership message will help you win more deals than capital-B branding, so do it first. If you can convince people that you are the technology leader, the market leader, and the vision leader, you are going to win a ton of deals in a growing category. Why wouldn’t you want to buy from someone who you thought was all three?
  • I view content marketing and thought leadership as demand generation, not branding. So that may be a source of confusion as well. Kellblog itself is demand generation and awareness generation for my serivces as a advisor or board member. It monetizes indirectly and is more demand generation than demand capture, but it works and I practice what I preach in this department.
  • A review of the two archetypal marketing messages: why buy one vs. why buy mine?
  • Lot’s wife‘s law (don’t look back) — why you should never communicate externally about smaller competitors.
  • Why, in competitive, the rule should be, “if they go low, we go lower” and not, “we go high.” Enterprise software sales is a full-contact sport. You need to train and arm your sellers to go play it. In a perfect world, they’re so well trained that they’re eagerly waiting what used to be the toughest attack points.
  • The other rule is, “when they go low, we get on the phone.” Never try to resolve competitor attacks via email. Use the attack as an opportunity to get on the phone and spend more time with the customer.
  • Why you should allocate enough budget to measure your external demand funnel: awareness, opinion, consideration, trial, purchase.
  • How to combat the age-old, “if we just had more at-bats we’d win more deals” or “nobody’s ever heard of us” claims from sales.

Thanks again to Amrita and Janessa for having me. The episode is here.

My Most Recent Appearance on 20VC with Harry Stebbings

Just a quick post to highlight my third and most recent appearance on 20VC with the amazing Harry Stebbings (Spotify, YouTube).

It is always, always a pleasure to speak with Harry. He’s such an effective interviewer that you quickly get into detail and stories that others miss. So you end up with very rich content, which in this case lasts significantly longer than 20 minutes. (More like 72, but who’s counting?)

In this episode we hit on a wide range of topics including:

  • The metrics that matter in SaaS today
  • Why CAC Payback is flawed and CAC ratio is better
  • Why you need to hire sales reps three-at-a-time (aka, modulo 3)
  • How to forecast in 2024 and in general (keyword: triangulate)
  • The biggest mistakes made in forecasting, and how sales management practices can confound the forecasting process
  • Why renewals are harder than ever to get (but alas easier to forecast)
  • What all this means for Customer Success (both the disicpline and the department)

I’ve embedded the video of the episode below. I hope you can make time to watch or listen to it. And thanks again to Harry for having me.

A Discussion of My 2024 Predictions on the AI and The Future of Work Podcast

Just a quick episode to highlight my recent appearance on Dan Turchin‘s AI and the Future Work podcast. In the episode, we discuss my 2024 predictions both in general and with an unsurprising spin towards AI and the future of work. I think this is our third year running in getting together to discuss my predictions.

If you don’t know Dan’s podcast, you should. It’s one of the longest running founder/CEO podcasts in Silicon Valley with approximately 300 total episodes, an overall 4.9 rating, and some great reviews including this one from none other than Ben Horowitz: ”I love this podcast. Great guests and great discussions about AI, ethics, technology, and entrepreneurship.”

Guests of note in the past year have included Arvind Jain (Glean), May Habib (Writer), Robert Plotkin (AI legal expert), Vijay Tella (Workato), Dr. John Boudreau (Cornell), Tom Wheeler (former FCC chair), Wade Foster (Zapier), and Meredith Broussard (NYU). 

In our discussion, Dan and I hit many topics, including:

  • My self-ratings on my 2023 predictions, including discussion of which are cycles, extrapolations, and pendulums.
  • A deeper dive on the “retain is the new add” 2023 prediction, looking at expansion ARR as a percent of new ARR as proof.
  • The post-truth world and AI’s impact on it through synthetically-generated content, including discussion on SEO and generative AI optimization.
  • History and future of algorithmically-generated feeds versus manual curation and how I sometimes find myself missing RSS.
  • Retrieval-augmented generation (RAG) and how its two key abilities (sourcing plus augmenting) help make generative AI much more appropriate for the enterprise.
  • AI climbing the proverbial hype cycle, including funding rounds and their structure; new value-based pricing and how much of AI-created value will be captured by vendors versus customers.
  • Fair use and large-language models (e.g., the New York Times complaint), including discussion of virtual SaaS expert pools such as SaaS GPT Lab.
  • Battery’s now somewhat famous slide on GTM efficiency, arguing that a sales team of 75 people armed with AI tools can support the same quota as a 110-person team without. Be ready for the board meeting where they ask about this slide!
  • The odds of both Dan and I attending the upcoming rumored performances of Dead & Company at The Sphere in Las Vegas.

I hope you make some time to listen to the episode. And thanks, Dan, for having me.