Messy Growth

AI is making it easier than ever to build software.That doesn’t mean it’s making it easier to build the right software.

In this episode of Messy Growth, I sit down with Cody Rogers, Chief Product Officer at Hubstaff and someone I worked with for years.This one was a little different because there’s history here. We’ve argued about customers, feature requests, sales, product decisions, probably annoyed each other more than once, and had a few drinks together along the way. Cody has spent more than eight years at Hubstaff, going from hands-on product work to leading the teams and systems that decide what gets built in the first place. And that makes him a pretty interesting person to ask what happens when AI suddenly makes building dramatically faster. We talk about why beautiful design is useless if you’re solving the wrong problem, how tools like Claude can help designers move faster while also making it dangerously easy to skip the thinking, and why taste, judgment and customer understanding matter more when everyone has access to the same tools. We also get into the relationship between sales and product — including why product teams say no to almost everything, why customers shouldn’t be allowed to design your roadmap, and what happens when teams stop trusting each other and disappear into silos. Cody also talks about what AI means for smaller SaaS competitors, why simply cloning a feature doesn’t recreate years of infrastructure, reliability and operational knowledge, and where established products still have a real moat. Later in the conversation, we get into the part of leadership that has almost nothing to do with product: hiring, managing people, letting people go, reorganizing teams, staying close to customers, and moving from a product mindset into thinking about the whole business. We also talk about remote work, why distributed companies need a completely different operating system, what Cody looks for when hiring, and why sometimes a four-minute personalized video can matter more than another polished résumé. One idea kept coming back throughout the episode:When building becomes cheap, deciding what deserves to be built becomes the real skill.Connect with CodyLinkedIn:   / codyrogers  

A like takes a second. A screenshot means someone wanted to keep it.Eli Sundelson describes his work as writing things people screenshot. I wanted to know what makes a piece of writing earn that and why so much business content gets the grammar, structure and hook right, then gives you nothing to remember.Before becoming a copywriter and ghostwriter at Big Brow Creative, Eli spent more than 20 years as a musician, including 16 teaching music. We talk about what that taught him about audiences, personality and helping someone express an idea.We also get into how he works with ghostwriting clients, the difference between shaping someone’s thoughts and inventing them, and why boredom and frustration can be useful parts of creative work. AI and LinkedIn come up throughout, along with the pressure to have something profound to post every day.Eli Sundelson / Big Brow Creative:https://bigbrowcreative.comHosted by Syed Asad | messygrowth.io Messy Growth is a series of honest conversations with founders, operators and people building businesses about the decisions, mistakes and experiences behind the work.

For years, agencies have added more people, more meetings, more approvals and more process.But does any of it actually make the work better?Marianne Kaiser spent nearly two decades inside creative and advertising agencies before deciding to build something very different.In this episode of Messy Growth, we talk about what she calls “process theater” - the layers of work that exist because “that’s how it’s always been done,” not necessarily because they create better outcomes for clients. Marianne shares the moment early in her career when she realized parts of the agency process had become disconnected from the actual work, why she kept seeing the same problems as she moved between agencies, and why eventually she decided to build Contrary Collective around smaller, senior-led teams instead. We get into why clients sometimes end up with 15 people on a call for a single email, the difference between real rigor and unnecessary bureaucracy, why agencies assign talent based on availability instead of fit, and what happens when creatives are trusted to actually do their jobs. We also talk about creativity in highly regulated industries like pharma and healthcare, why regulation can expose weak creative thinking faster, and how Marianne’s own experience as a patient shaped the way she approaches healthcare work. Later in the conversation, we get into agency culture, silos, timesheets, compensation, creative leadership, and what Marianne hopes the industry stops doing simply because it has always been done that way.One question kept coming up throughout the conversation:What’s actually required here and what are we only doing because nobody stopped to question it?Connect with MarianneLinkedIn:   / mariannekaiser  Website: bequitecontrary.com

Creative agencies run on freelance talent, yet many still manage those relationships with spreadsheets, Slack messages, and forgotten Rolodexes.After 17 years inside creative agencies, former VP / Group Creative Director Melissa Withorn got tired of seeing the same problem everywhere. So she built Cast, a platform designed to help agencies manage and discover freelance creative talent.In this episode of Messy Growth, Melissa talks about:• Leaving a senior creative career and becoming a first-time founder at 38• Why agencies are still using outdated systems to manage freelancers• Building Cast’s MVP with Lovable and AI• The danger of vibe coding without talking to customers• Finding the right ICP and resisting feature requests• Building a product around real customer feedback• Why freelancers should be compensated for their networks• Building a company in public• The reality of balancing entrepreneurship, family, and lifeMost importantly, Melissa shares what she’s learned about taking 17 years of industry experience and turning it into a startup.Guest: Melissa WithornCompany: Cast — castcreative.ioCommunity: Feral Founders Club

AI has made creating things ridiculously easy.You can write the article, make the image, build the app, generate the code, create the campaign - all before breakfast.And somehow, a lot of what comes out of it sounds exactly the same.Same ideas. Same LinkedIn posts. Same language. Same GPT voice.So I wanted to talk to someone who spends a lot of her time actually working with AI, marketers and teams building with these tools.Julia de Oliveira Camargo and I got into what happens when production stops being the bottleneck.We talked about why perspective matters more than ever, why most companies are still obsessed with producing more stuff, where AI agents actually make sense (and where they don’t), why boring businesses might be the biggest winners from AI, and why marketers may have a bigger advantage in this next phase than they realize.We also got into personal branding, long-form vs short-form content, Claude vs ChatGPT, the future of marketing, and why knowing what you actually want might be one of the most valuable skills left.Good conversation. Some strong opinions. A few fights with ChatGPT/Claude.Hope you enjoy it.

What happens when you believe in yourself before there’s any evidence that you’re right?Anjanette Carter built a seven-figure copywriting and ghostwriting business, a growing personal brand, a bestselling Substack newsletter, and The Breadboard job board.But the interesting part isn’t the success.It’s what happened when things didn’t work.In this episode of Messy Growth, we talk about what it actually means to bet on yourself, how to know when persistence turns into delusion, why going viral is overrated, and why you don’t need a massive audience to build a real business.Anjeanette also shares why she believes builders should stop boxing themselves into one identity, why consistency matters more than chasing viral moments, and what she’s learned from failing along the way.And yes, we talk about the uncomfortable part of entrepreneurship that most people leave out:Sometimes you work your ass off and it still doesn’t work.So what do you do then?In this episode:

• The difference between confidence and delusion
• When persistence becomes a problem
• How to know when it’s time to change direction
• Why “never give up” is terrible advice on its own
• Why going viral isn’t the same as building a business
• How to build an audience without chasing millions of followers
• Why consistency beats virality
• How Anjanette built a seven-figure copywriting business
• Building a personal brand before you actually need one
• Why you don’t have to be just one thing
• The future of newsletters, content and personal brands
• Why builders keep building
• And the uncomfortable reality of entrepreneurship

One line from the conversation stuck with me:“The suck won’t last forever.”If you’re building something right now and wondering whether you’re crazy for continuing, this one’s for you.

What happens when you believe in yourself before there’s any evidence that you’re right?

Anjeanette Carter built a seven-figure copywriting and ghostwriting business, a growing personal brand, a bestselling Substack newsletter, and The Breadboard job board.

But the interesting part isn’t the success.

It’s what happened when things didn’t work.

In this episode of Messy Growth, we talk about what it actually means to bet on yourself, how to know when persistence turns into delusion, why going viral is overrated, and why you don’t need a massive audience to build a real business.

Anjanette also shares why she believes builders should stop boxing themselves into one identity, why consistency matters more than chasing viral moments, and what she’s learned from failing along the way.

And yes, we talk about the uncomfortable part of entrepreneurship that most people leave out:

Sometimes you work your ass off and it still doesn’t work.

So what do you do then?

• The difference between confidence and delusion
• When persistence becomes a problem
• How to know when it’s time to change direction
• Why “never give up” is terrible advice on its own
• Why going viral isn’t the same as building a business
• How to build an audience without chasing millions of followers
• Why consistency beats virality
• How Anjanette built a seven-figure copywriting business
• Building a personal brand before you actually need one
• Why you don’t have to be just one thing
• The future of newsletters, content and personal brands
• Why builders keep building
• And the uncomfortable reality of entrepreneurship

One line from the conversation stuck with me:

“The suck won’t last forever.”

If you’re building something right now and wondering whether you’re crazy for continuing, this one’s for you.

In this episode:

Everyone’s talking about AI but very few people are actually using it to create content, grow an audience, or build a business.In this episode of Messy Growth, I sit down with Dustin Hauer, VP, AI educator, and creator with more than 31 million LinkedIn impressions, to talk about AI, ChatGPT, Claude, LinkedIn growth, content marketing, personal branding, and practical AI workflows that actually work.Instead of chasing every new AI tool, Dustin shares how he uses AI every day to create content faster, build systems, grow multiple online brands, and stay ahead without becoming another “AI influencer.”Whether you’re a founder, marketer, creator, or business leader, this conversation will help you separate AI hype from practical execution.In this episode:

• How Dustin generated 31M+ LinkedIn impressions
• Why most people are using ChatGPT the wrong way
• How to build content systems with AI
• The LinkedIn strategy that’s working in 2026
• Why infographics outperform most content formats
• Prompt engineering that actually saves time
• How to build a personal brand without posting 24/7
• Why experimentation beats perfection
• The biggest mistakes creators make with AI
• Where AI is heading next and what’s just hype

If you enjoyed this episode, subscribe to Messy Growth for weekly conversations with founders, operators, and leaders building high-growth SaaS companies.

We’re supposedly more connected than we’ve ever been.So why are so many people lonely?This week’s conversation completely changed how I think about community, networking, AI companions, social media, and why so many events fail to create real human connection.Maggie Arai has spent years helping brands and creators turn online audiences into real communities through in-person experiences. We talked about why adults struggle to make friends, why boring networking events refuse to die, whether AI companions are making loneliness worse, and why the future might actually belong to people who can bring others together.Some of my favorite moments:• Why “networking” feels so awkward for most people.• The real reason adults struggle to make friends.• AI companions, therapy bots, and the unintended consequences nobody is talking about.• Why online communities rarely become real communities.• The biggest mistake brands make when they host events.• Why human connection might become even more valuable in the age of AI.If you’ve ever felt like social media gives you more notifications than relationships, I think you’ll enjoy this one.Connect with Maggie:   / maggie-arai  

Every AI startup claims to be revolutionizing something.Every homepage says it’s AI-powered.Every pitch deck sounds like it was written by the same person.So why do so many smart companies struggle to explain what they actually do?In this episode of Messy Growth, I sat down with positioning strategist Simon Schmitz to unpack why messaging not product is often the biggest reason startups fail to stand out.We talk about why founders overcomplicate simple ideas, why adding more features usually makes your positioning worse, how politics shaped Simon’s approach to messaging, and why most companies are afraid to make the one decision that actually creates clarity.If you’ve ever looked at a startup website and thought, “I still have no idea what this company does,” this episode is for you.We cover:

• Why every AI startup sounds identical
• The biggest messaging mistakes founders make
• Why customers don’t care about your features first
• The fear of niching down (and why it’s killing growth)
• How better positioning leads to better sales
• Why clarity beats cleverness every time
• The hidden cost of trying to appeal to everyone

If you enjoyed this conversation, consider subscribing to Messy Growth for weekly conversations with founders, operators and GTM leaders building and scaling great businesses.