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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 delusionWhen persistence becomes a problemHow to know when it’s time to change directionWhy “never give up” is terrible advice on its ownWhy going viral isn’t the same as building a businessHow to build an audience without chasing millions of followersWhy consistency beats viralityHow Anjanette built a seven-figure copywriting businessBuilding a personal brand before you actually need oneWhy you don’t have to be just one thingThe future of newsletters, content and personal brandsWhy builders keep buildingAnd the uncomfortable reality of entrepreneurshipOne 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.

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 impressionsWhy most people are using ChatGPT the wrong wayHow to build content systems with AIThe LinkedIn strategy that’s working in 2026Why infographics outperform most content formatsPrompt engineering that actually saves timeHow to build a personal brand without posting 24/7Why experimentation beats perfectionThe biggest mistakes creators make with AIWhere AI is heading next and what’s just hypeIf 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 identicalThe biggest messaging mistakes founders makeWhy customers don’t care about your features firstThe fear of niching down (and why it’s killing growth)How better positioning leads to better salesWhy clarity beats cleverness every timeThe hidden cost of trying to appeal to everyoneIf you enjoyed this conversation, consider subscribing to Messy Growth for weekly conversations with founders, operators and GTM leaders building and scaling great businesses.

Everyone says you need a personal brand.Almost nobody tells you how to build one without sounding like everyone else.In this episode of Messy Growth, I sit down with Jillian Richardson, founder of Make LinkedIn Weird and one of the most sought-after LinkedIn ghostwriters. We talk about why LinkedIn has become a sea of AI-generated corporate speak, what actually makes people memorable, and why authenticity is much harder than simply “being yourself.”We also dive into:• Why most LinkedIn content feels fake• The truth about ghostwriting for CEOs• How personal brands are really built• Why funny content often outperforms “professional” content• AI, authenticity, and the future of LinkedIn• The biggest mistakes founders make online• Building authority without becoming another corporate cloneWhether you’re a founder, executive, marketer, creator, or simply trying to stand out online, this conversation will change how you think about content.

Everyone is chasing algorithms.More posts.More AI.More hacks.More engagement tricks.But what if we’ve been solving the wrong problem all along?In this episode of Messy Growth, I sit down with Carmen Vicente -LinkedIn Top Voice, marketing leader, and one of the sharpest thinkers in B2B social to unpack what actually drives attention and trust today.We talk about why going viral can be a curse, how AI is reshaping social platforms, why founder-led content often fails, and what companies completely misunderstand about building an audience.If you create content, lead a company, work in marketing, or simply wonder where the internet is heading, this conversation is for you.We cover:* Why trust is replacing attention as the real competitive advantage* The future of LinkedIn and AI-powered algorithms* Why consistency isn’t the whole story* Why founder content often feels fake* The hidden cost of chasing virality* What great B2B content actually looks like* Why social media keeps us scrolling—even when we’re exhausted* Where AI is taking marketing over the next few years

Everyone talks about digital transformation, AI, fintech, and innovation. But why do so many transformation projects fail?In this episode of Messy Growth, I sit down with Tom Hill, CEO of Zyntrix and former retail transformation leader at Sainsbury’s, Poundland, KFC, and SSP.After spending nearly two decades on both the operational and executive sides of retail, Tom shares why businesses don’t actually care about technology - they care about outcomes.We discuss:• Why great products still struggle to sell• Why resistance to change usually starts in the boardroom—not on the front line• The future of Open Banking and Pay by Bank• Why loyalty programs often fail• What retailers get wrong about customer experience• AI hype vs solving real business problems• Lessons from leading transformation inside large enterprisesWhether you’re a founder, product leader, sales executive, or operator, this conversation is packed with practical lessons on building products people actually adopt.About Tom HillTom Hill is the CEO of Zyntrix, a fintech company focused on Open Banking, digital identity, and loyalty. Before becoming CEO, he spent nearly two decades leading retail operations and digital transformation across major brands including Sainsbury’s, Poundland, KFC, and SSP.

Everyone is creating content.Founders post every day. Companies publish blogs. AI can write almost anything in seconds.So why is trust harder to earn than ever?In this episode of Messy Growth, I sit down with Wendy Jacobson, founder of Incredible Content, who’s spent nearly two decades helping B2B companies turn expertise into credibility.We talk about why going viral is often overrated, why most content fails to bring customers, how AI is changing writing, and why the businesses that win over the next decade won’t necessarily create more content - they’ll create more trust.If you’re a founder, marketer, sales leader, or building a B2B business, this conversation is packed with practical lessons you can apply immediately.We cover:• Why viral content rarely creates great customers• The biggest mistake companies make with content• How to build credibility instead of chasing engagement• AI, authenticity, and what still separates great writing• Why case studies fail (and how to make people actually care)• The long game behind content that drives real businessConnect with Wendy: https://www.linkedin.com/in/wjacobson/

Everyone is building.AI has made launching products easier than ever, but building something is no longer the hard part. Getting people to care is.In this episode of Messy Growth, I sit down with Basia Derkowska, Fractional CMO and Go-To-Market Advisor, to talk about what actually happens after you’ve built the product.We cover why “go-to-market” suddenly became everyone’s favorite buzzword, why founders often freeze instead of moving, how to think about distribution before spending money on marketing, and what separates companies that grow from the ones that quietly disappear.We also dive into:* Why founders should stop trying to do everything at once* The difference between freelancers, fractional leaders and full-time executives* How to know if you’re ready to go fractional* Why understanding your customers beats any AI prompt* Why great products still fail* Building a personal brand without becoming another LinkedIn cliché* How AI is changing marketing and what it can’t replaceIf you’re building a startup, thinking about going fractional, working in B2B SaaS, or simply trying to figure out how to stand out in an increasingly noisy world, this conversation is for you.Connect with Basia: https://www.linkedin.com/in/barbara-derkowska/

Most founders think product-market fit looks like a full calendar, pilot customers, and growing interest.They’re wrong.In this episode of Messy Growth, I sit down with product marketing leader Elina Bazinas to unpack why attention is not the same as traction, how startups confuse interest for demand, and why positioning is becoming the most important competitive advantage in the AI era.We discuss:• The biggest product-market fit misconceptions founders make• Why most AI products struggle after the demo• The difference between attention and genuine customer pull• Why positioning matters more than features• How great product launches are won before launch day• The role of trust in modern B2B buying• Why AI is making strong product marketing more valuable, not less• How founders can tell if they truly understand their customers• The one question every founder should answer before trying to scaleIf you’re building a SaaS company, working in product, marketing, sales, or trying to figure out why growth has stalled, this conversation is packed with practical insights.