Burn The Map: AI Is Making SaaS Weird, Pricing Hard, and Authenticity Non-Negotiable w/ Kelly Pronek

Burn The Map: AI Is Making SaaS Weird, Pricing Hard, and Authenticity Non-Negotiable w/ Kelly Pronek

In This Episode: We sit down with Kelly Pronek, go-to-market operator, pricing obsessive, and former Pricefx leader, for a conversation that starts with AI tooling and quickly turns into something bigger: how modern software businesses are being rebuilt in real time. Kelly breaks down why pricing is still one of the hardest jobs in business, why most companies are rolling out AI like a preschool teacher dumping instruments on the floor, and why the real value in the next wave of software may not be the platform at all — it may be the taste, judgment, and specificity of the people using it. This one moves from usage-based pricing and CRM sprawl to dyslexia, neurodivergence, implementation chaos, AI "employees" with hangovers, and the growing premium on real voice in a market flooded with sameness. It's a sharp conversation about what happens when software gets easier to build, harder to differentiate, and a lot more personal. What We Cover: * Why pricing is part science, part art, and still brutally difficult * How AI is pushing SaaS from standardization back toward bespoke businesses * The case for hybrid pricing models: subscription plus consumption * Why performance-based pricing sounds great — until implementation gets in the way * How small teams can now build internal tools that used to require enterprise vendors * Why content created by AI still needs a human with taste, nuance, and a point of view * Neurodivergence, learning styles, and how AI may unlock better ways to think and communicate * Why authenticity is becoming more valuable as every company starts to sound the same Guest Bio: Kelly Pronek is a go-to-market and operations leader with deep experience across pricing, SaaS, revenue operations, and emerging business models. She previously spent nearly seven years at Pricefx and now works with startups and operators on go-to-market structure, pricing strategy, and practical AI adoption. Kelly is especially interested in how businesses can use AI to reduce friction, preserve authenticity, and build smarter systems without losing the human signal. Enjoy the episode. This show is brought to you by Wrench.ai [http://wrench.ai]. Follow Dan: LinkedIn: https://www.linkedin.com/in/danbaird/ [https://www.linkedin.com/in/danbaird/]X: https://x.com/mrdanbaird [https://x.com/mrdanbaird] Follow Kelly: LinkedIn: https://www.linkedin.com/in/kpronek/ [https://www.linkedin.com/in/kpronek/] Follow the Pod: YouTube: https://www.youtube.com/@burnthemappodcast [https://www.youtube.com/@burnthemappodcast]Twitter/X: https://x.com/BurnTheMapPod [https://x.com/BurnTheMapPod]Instagram: https://www.instagram.com/burnthemappodcast/ [https://www.instagram.com/burnthemappodcast/]TikTok:https://www.tiktok.com/@burnthemappodcast [https://www.tiktok.com/@burnthemappodcast]BlueSky: https://bsky.app/profile/burnthemappodcast.bsky.social [https://bsky.app/profile/burnthemappodcast.bsky.social] Selected Links From This Episode: * Burn The Map website: https://burnthemapshow.com/ [https://burnthemapshow.com/] * Wrench.ai: https://wrench.ai [https://wrench.ai/] People and Organizations Mentioned: * Kelly Pronek * Dan Baird * Pricefx * Claude * OpenAI * HubSpot * Klaviyo * Notion * N8N * Apollo * NotebookLM Show Notes & Timestamps: * 00:08 — Dan and Kelly open on pricing, AI, and why both are harder than they look * 01:38 — Kelly on leaving Pricefx but staying obsessed with pricing * 03:05 — AI token addiction, internal adoption chaos, and the question nobody asks: is this producing anything? * 06:34 — "At least it tries": what AI changes for average vs. excellent workers * 10:03 — Where people misuse AI most: content creation without human taste * 12:01 — Writing style tells on you: checkboxes, em dashes, and the missing dot-dot-dot * 13:27 — AI as a thinking partner, not just a writing engine * 19:31 — Why neurodivergent people may have an edge in AI-native workflows * 21:33 — Back to pricing: collapsing SaaS moats, custom tools, and the return of bespoke systems * 23:08 — Why data matters more than software, and why most people won't use a CRM the way you hope * 26:35 — Vibe coding, messy stacks, and the back-end nightmares nobody wants to talk about * 29:41 — Kelly's path into pricing science and why smaller businesses have always had to price with less certainty * 32:04 — How AI may make pricing software and pricing research more accessible * 37:30 — AI as a force multiplier for technical founders who were never natural marketers * 39:12 — Brand, culture, and why inauthentic companies feel like theft * 41:54 — Kelly's startup pricing framework: know your costs, know the market, then price with conviction * 43:37 — Hybrid and performance pricing: appealing in theory, messy in practice * 45:22 — Implementation is the real bottleneck * 48:08 — Which tools still matter when everyone's stack starts to blur together * 49:33 — Kelly's favorite tools right now: Claude cowork, NotebookLM, and now Whisper * 56:41 — Why AI may create more room for actual human connection, not less * 57:55 — Most companies are still treating AI like unstructured playtime * 59:36 — Decentralized AI, compute limits, and a fragile hope for moral infrastructure

Burn The Map: Why AI Won't Fix a Leadership Problem w/ Angeley Mullins

In This Episode: We talk to Angeley Mullins about what it actually takes to scale in a market where the ground keeps moving under your feet. She gets into the brutal gap between founder-led sales and real product-market fit, why most teams think they have a tech problem when they actually have a leadership problem, and why AI is exposing weak judgment faster than ever. From brand and content to org design and digital leadership, this conversation is a sharp look at what modern go-to-market really demands when speed, scrutiny, and automation are all turned up to eleven. What We Cover: * Why founder-led sales can create the illusion of product-market fit * Why brand is still the original revenue driver, not some fluffy side project * How AI is compressing product cycles and forcing leaders to move faster * Why firing content teams right now is a spectacularly bad idea * The shift from bloated teams to tiny groups of high-leverage operators * Why "a tool is not a strategy" — and definitely not a leadership plan Guest Bio: Angeley Mullins is a go-to-market leader, advisor, and operator who has helped scale seven companies across big tech and high-growth startups, including businesses at IPO and unicorn stages. Based in Germany, she works at the intersection of AI, revenue, brand, and digital transformation, helping founders and CEOs build smarter, faster, and with a lot less delusion. Enjoy the episode. This show is brought to you by Wrench.ai [http://wrench.ai]. Follow Dan: LinkedIn:https://www.linkedin.com/in/danbaird/ [https://www.linkedin.com/in/danbaird/]X: https://x.com/mrdanbaird [https://x.com/mrdanbaird] Follow Angeley: LinkedIn: https://www.linkedin.com/in/angeleymullins/ [https://www.linkedin.com/in/angeleymullins/] Instagram: https://www.instagram.com/angeleymullins/ [https://www.instagram.com/angeleymullins/] Follow the Pod: YouTube: https://www.youtube.com/@burnthemappodcast [https://www.youtube.com/@burnthemappodcast]Twitter/X: https://x.com/BurnTheMapPod [https://x.com/BurnTheMapPod]Instagram: https://www.instagram.com/burnthemappodcast/ [https://www.instagram.com/burnthemappodcast/]TikTok: https://www.tiktok.com/@burnthemappodcast [https://www.tiktok.com/@burnthemappodcast]BlueSky:https://bsky.app/profile/burnthemappodcast.bsky.social [https://bsky.app/profile/burnthemappodcast.bsky.social] Selected Links From This Episode: * Angeley Mullins website: https://angeleymullins.org [https://angeleymullins.org/] * Burn The Map: https://burnthemapshow.com/ [https://burnthemapshow.com/] * Wrench.ai: https://wrench.ai [https://wrench.ai/] * The Revenue Divide Article: https://thenextweb.com/news/the-revenue-divide-us-vs-eu-leadership [https://thenextweb.com/news/the-revenue-divide-us-vs-eu-leadership] People and Organizations Mentioned: * Ninox * Miro * Vanta * HubSpot * Klaviyo * Loveable * Synthesia * Clay * Anthropic * Google * Gemini * Microsoft ShowNotes & Timestamps: * 00:08 — Why GTM is harder than most people admit * 01:32 — The real danger zone: fake product-market fit * 03:03 — Why AI has made software competition brutally fast * 04:24 — Brand isn't fluff — it's the original revenue driver * 06:23 — How to rank in the GPT era: brand + content * 08:24 — Why old decision cycles are dying * 10:27 — Automating your own job before AI does it for you * 11:35 — The hidden failure mode: AI throughput that isn't real * 13:08 — AI, Google Maps, and the erosion of critical thinking * 15:35 — What AI might fix in healthcare — and break in human judgment * 17:02 — Why self-awareness and ego control define good leadership * 20:43 — Why off-the-shelf CRMs rarely stay off the shelf * 21:48 — Investors now want smaller, faster companies * 25:06 — The rise of digital leaders and the death of bloated GTM orgs * 28:33 — Why AI adoption is a huge consulting category now * 29:39 — Which operators Angeley watches as the market shifts * 31:25 — The coming white-collar displacement wave * 34:20 — Europe vs. the U.S.: the real issue is culture, not tech * 36:22 — Why Angeley thinks Asia is the real future

Burn The Map: Why AI Won't Fix a Leadership Problem w/ Angeley Mullins

In This Episode: We talk to Angeley Mullins about what it actually takes to scale in a market where the ground keeps moving under your feet. She gets into the brutal gap between founder-led sales and real product-market fit, why most teams think they have a tech problem when they actually have a leadership problem, and why AI is exposing weak judgment faster than ever. From brand and content to org design and digital leadership, this conversation is a sharp look at what modern go-to-market really demands when speed, scrutiny, and automation are all turned up to eleven. What We Cover: * Why founder-led sales can create the illusion of product-market fit * Why brand is still the original revenue driver, not some fluffy side project * How AI is compressing product cycles and forcing leaders to move faster * Why firing content teams right now is a spectacularly bad idea * The shift from bloated teams to tiny groups of high-leverage operators * Why "a tool is not a strategy" — and definitely not a leadership plan Guest Bio: Angeley Mullins is a go-to-market leader, advisor, and operator who has helped scale seven companies across big tech and high-growth startups, including businesses at IPO and unicorn stages. Based in Germany, she works at the intersection of AI, revenue, brand, and digital transformation, helping founders and CEOs build smarter, faster, and with a lot less delusion. Enjoy the episode. This show is brought to you by Wrench.ai [http://wrench.ai]. Follow Dan: LinkedIn:https://www.linkedin.com/in/danbaird/ [https://www.linkedin.com/in/danbaird/]X: https://x.com/mrdanbaird [https://x.com/mrdanbaird] Follow Angeley: LinkedIn: https://www.linkedin.com/in/angeleymullins/ [https://www.linkedin.com/in/angeleymullins/] Instagram: https://www.instagram.com/angeleymullins/ [https://www.instagram.com/angeleymullins/] Follow the Pod: YouTube: https://www.youtube.com/@burnthemappodcast [https://www.youtube.com/@burnthemappodcast]Twitter/X: https://x.com/BurnTheMapPod [https://x.com/BurnTheMapPod]Instagram: https://www.instagram.com/burnthemappodcast/ [https://www.instagram.com/burnthemappodcast/]TikTok: https://www.tiktok.com/@burnthemappodcast [https://www.tiktok.com/@burnthemappodcast]BlueSky:https://bsky.app/profile/burnthemappodcast.bsky.social [https://bsky.app/profile/burnthemappodcast.bsky.social] Selected Links From This Episode: * Angeley Mullins website: https://angeleymullins.org [https://angeleymullins.org/] * Burn The Map: https://burnthemapshow.com/ [https://burnthemapshow.com/] * Wrench.ai: https://wrench.ai [https://wrench.ai/] * The Revenue Divide Article: https://thenextweb.com/news/the-revenue-divide-us-vs-eu-leadership [https://thenextweb.com/news/the-revenue-divide-us-vs-eu-leadership] People and Organizations Mentioned: * Ninox * Miro * Vanta * HubSpot * Klaviyo * Loveable * Synthesia * Clay * Anthropic * Google * Gemini * Microsoft ShowNotes & Timestamps: * 00:08 — Why GTM is harder than most people admit * 01:32 — The real danger zone: fake product-market fit * 03:03 — Why AI has made software competition brutally fast * 04:24 — Brand isn't fluff — it's the original revenue driver * 06:23 — How to rank in the GPT era: brand + content * 08:24 — Why old decision cycles are dying * 10:27 — Automating your own job before AI does it for you * 11:35 — The hidden failure mode: AI throughput that isn't real * 13:08 — AI, Google Maps, and the erosion of critical thinking * 15:35 — What AI might fix in healthcare — and break in human judgment * 17:02 — Why self-awareness and ego control define good leadership * 20:43 — Why off-the-shelf CRMs rarely stay off the shelf * 21:48 — Investors now want smaller, faster companies * 25:06 — The rise of digital leaders and the death of bloated GTM orgs * 28:33 — Why AI adoption is a huge consulting category now * 29:39 — Which operators Angeley watches as the market shifts * 31:25 — The coming white-collar displacement wave * 34:20 — Europe vs. the U.S.: the real issue is culture, not tech * 36:22 — Why Angeley thinks Asia is the real future

Burn The Map: Let the AI Do the Work, Let Humans Be Human w/ Chris Singel

In This Episode: We talk to Chris Singel about comedy, marketing, AI, media trust, and the quietly unnerving future of work. Chris has spent more than 20 years making people laugh — teaching improv, sketch, and stand-up, and spending nearly a decade at Funny or Die — so he's got a sharp read on what actually lands with an audience versus what just tries too hard. His core idea: you probably can't teach someone to be funny, but you absolutely can help them understand what they find funny and how to make other people come along for the ride. From there, the conversation gets bigger fast. We get into why crowd work is exploding, why authenticity is both powerful and dangerously easy to fake, and how AI is already good enough to change the way creative work gets made. Chris doesn't do the usual techno-utopian fantasy or anti-AI panic spiral. He's more interesting than that. He's asking the messier question: if machines increasingly handle the labor, what exactly are humans supposed to do with themselves — and are we ready for the answer? What We Cover: * Why comedy isn't magic, but it also isn't a formula you can copy-paste * The difference between being shocking and being actually funny * What stand-up teaches you about audiences, iteration, and killing your darlings * Why comedians are often better listeners than the people interviewing them * How comedy mechanics show up in branding, virality, and marketing * What AI can already do well in writing and creative work — and where it still falls flat * Why hyper-personalized media is coming fast, and why that's both useful and creepy * The future of work, post-scarcity fantasies, and whether humans will know what matters when efficiency wins Guest Bio: Chris Singel is a marketer, comedian, former news producer, and founder of Delta Digital Agency. He spent nearly a decade at Funny or Die and has been performing and teaching comedy for over 20 years across improv, sketch, and stand-up. His work sits at the intersection of storytelling, audience psychology, and AI — helping brands communicate better while also exploring what happens when the machines get good enough to join the writer's room. Enjoy the episode. This show is brought to you by Wrench.ai [http://wrench.ai]. Follow Dan: LinkedIn: https://www.linkedin.com/in/danbaird/ [https://www.linkedin.com/in/danbaird/]X: https://x.com/mrdanbaird [https://x.com/mrdanbaird] Follow Chris: LinkedIn: https://www.linkedin.com/in/csingel/ [https://www.linkedin.com/in/csingel/] Instagram: https://www.instagram.com/csingel/ [https://www.instagram.com/csingel/] Follow the Pod: YouTube: https://www.youtube.com/@burnthemappodcast [https://www.youtube.com/@burnthemappodcast]Twitter/X: https://x.com/BurnTheMapPod [https://x.com/BurnTheMapPod]Instagram: https://www.instagram.com/burnthemappodcast/ [https://www.instagram.com/burnthemappodcast/]TikTok: https://www.tiktok.com/@burnthemappodcast [https://www.tiktok.com/@burnthemappodcast]BlueSky: https://bsky.app/profile/burnthemappodcast.bsky.social [https://bsky.app/profile/burnthemappodcast.bsky.social] Selected Links From This Episode: * Delta Digital Agency: https://deltadigitalagency.com/ [https://deltadigitalagency.com/] * Wrench.ai: https://wrench.ai [https://wrench.ai/] * Burn The Map: https://burnthemapshow.com/ [https://burnthemapshow.com/] People and Organizations Mentioned: * Funny or Die * Delta Digital Agency * Wrench.ai * Zach Galifianakis * Anthony Jeselnik * Mitch Hedberg * Norm Macdonald * Tig Notaro * Dave Chappelle * Joe Rogan * Theo Von * CNN * Fox News * Tucker Carlson * Jon Stewart * Rupert Murdoch * TJ Miller * Rory Scovel * Andy Haynes * Danny Rouhier * Chris Farley * Mike Myers Show Notes & Timestamps: 01:45 — Misdirection, offensive comedy, and the theory of benign violation 04:10 — Improv terminology, status, character, physicality, and Chris Farley's genius 05:21 — First-time stand-up advice: getting your first laughs and surviving your second set 06:12 — Is there a formula for comedy? Chappelle, structure, repetition, and art vs. mechanics 08:02 — What muscles comedy builds: audience awareness, restructuring, and point of view 09:39 — The hardest comedians to copy: Emo Philips, Mitch Hedberg, Norm Macdonald 10:57 — Shock value vs. actual craft, plus Tig Notaro's layered joke construction 12:12 — How comedy thinking applies to marketing, virality, and ad creative 13:08 — Funny or Die's volume game: make 12 things, let 6 flop, and scale what works 15:38 — Why comedians are strong listeners, and why crowd work dominates social clips 16:32 — Comedy podcasts, politics, and why comics now have media-scale influence 17:19 — Dave Chappelle, misinterpretation, and the risks of being treated as a truth source 18:55 — Trust, institutions, and the weird migration from journalism to personality media 21:21 — News ownership, incentives, and the corporate logic behind public narratives 23:53 — AI video, synthetic content, and the terrifying rise of actually watchable slop 27:45 — How AI changes creative work: prompting, iteration, and removing human middlemen 31:04 — Personalized marketing, emotional targeting, and the future of one-to-one persuasion 33:54 — AGI, recursive intelligence, and why the sci-fi future feels uncomfortably close 36:03 — What humans are still "needed" for when work gets automated 39:25 — AI, time freedom, and the trap of using saved time to just do more work 40:09 — Eisenhower matrices, family priorities, and deciding what actually matters 41:24 — What Chris is best at: persuasion, performance, and reading the room 43:08 — When persuasion backfires: scope creep, people pleasing, and values drift 47:39 — Chris's AI book experiments and what machine "thought" reveals about human anxiety 53:16 — Delta Digital Agency, how Chris works, and where to follow him online

Burn The Map: Let the AI Do the Work, Let Humans Be Human w/ Chris Singel

In This Episode: We talk to Chris Singel about comedy, marketing, AI, media trust, and the quietly unnerving future of work. Chris has spent more than 20 years making people laugh — teaching improv, sketch, and stand-up, and spending nearly a decade at Funny or Die — so he's got a sharp read on what actually lands with an audience versus what just tries too hard. His core idea: you probably can't teach someone to be funny, but you absolutely can help them understand what they find funny and how to make other people come along for the ride. From there, the conversation gets bigger fast. We get into why crowd work is exploding, why authenticity is both powerful and dangerously easy to fake, and how AI is already good enough to change the way creative work gets made. Chris doesn't do the usual techno-utopian fantasy or anti-AI panic spiral. He's more interesting than that. He's asking the messier question: if machines increasingly handle the labor, what exactly are humans supposed to do with themselves — and are we ready for the answer? What We Cover: * Why comedy isn't magic, but it also isn't a formula you can copy-paste * The difference between being shocking and being actually funny * What stand-up teaches you about audiences, iteration, and killing your darlings * Why comedians are often better listeners than the people interviewing them * How comedy mechanics show up in branding, virality, and marketing * What AI can already do well in writing and creative work — and where it still falls flat * Why hyper-personalized media is coming fast, and why that's both useful and creepy * The future of work, post-scarcity fantasies, and whether humans will know what matters when efficiency wins Guest Bio: Chris Singel is a marketer, comedian, former news producer, and founder of Delta Digital Agency. He spent nearly a decade at Funny or Die and has been performing and teaching comedy for over 20 years across improv, sketch, and stand-up. His work sits at the intersection of storytelling, audience psychology, and AI — helping brands communicate better while also exploring what happens when the machines get good enough to join the writer's room. Enjoy the episode. This show is brought to you by Wrench.ai [http://wrench.ai]. Follow Dan: LinkedIn: https://www.linkedin.com/in/danbaird/ [https://www.linkedin.com/in/danbaird/]X: https://x.com/mrdanbaird [https://x.com/mrdanbaird] Follow Chris: LinkedIn: https://www.linkedin.com/in/csingel/ [https://www.linkedin.com/in/csingel/] Instagram: https://www.instagram.com/csingel/ [https://www.instagram.com/csingel/] Follow the Pod: YouTube: https://www.youtube.com/@burnthemappodcast [https://www.youtube.com/@burnthemappodcast]Twitter/X: https://x.com/BurnTheMapPod [https://x.com/BurnTheMapPod]Instagram: https://www.instagram.com/burnthemappodcast/ [https://www.instagram.com/burnthemappodcast/]TikTok: https://www.tiktok.com/@burnthemappodcast [https://www.tiktok.com/@burnthemappodcast]BlueSky: https://bsky.app/profile/burnthemappodcast.bsky.social [https://bsky.app/profile/burnthemappodcast.bsky.social] Selected Links From This Episode: * Delta Digital Agency: https://deltadigitalagency.com/ [https://deltadigitalagency.com/] * Wrench.ai: https://wrench.ai [https://wrench.ai/] * Burn The Map: https://burnthemapshow.com/ [https://burnthemapshow.com/] People and Organizations Mentioned: * Funny or Die * Delta Digital Agency * Wrench.ai * Zach Galifianakis * Anthony Jeselnik * Mitch Hedberg * Norm Macdonald * Tig Notaro * Dave Chappelle * Joe Rogan * Theo Von * CNN * Fox News * Tucker Carlson * Jon Stewart * Rupert Murdoch * TJ Miller * Rory Scovel * Andy Haynes * Danny Rouhier * Chris Farley * Mike Myers Show Notes & Timestamps: 01:45 — Misdirection, offensive comedy, and the theory of benign violation 04:10 — Improv terminology, status, character, physicality, and Chris Farley's genius 05:21 — First-time stand-up advice: getting your first laughs and surviving your second set 06:12 — Is there a formula for comedy? Chappelle, structure, repetition, and art vs. mechanics 08:02 — What muscles comedy builds: audience awareness, restructuring, and point of view 09:39 — The hardest comedians to copy: Emo Philips, Mitch Hedberg, Norm Macdonald 10:57 — Shock value vs. actual craft, plus Tig Notaro's layered joke construction 12:12 — How comedy thinking applies to marketing, virality, and ad creative 13:08 — Funny or Die's volume game: make 12 things, let 6 flop, and scale what works 15:38 — Why comedians are strong listeners, and why crowd work dominates social clips 16:32 — Comedy podcasts, politics, and why comics now have media-scale influence 17:19 — Dave Chappelle, misinterpretation, and the risks of being treated as a truth source 18:55 — Trust, institutions, and the weird migration from journalism to personality media 21:21 — News ownership, incentives, and the corporate logic behind public narratives 23:53 — AI video, synthetic content, and the terrifying rise of actually watchable slop 27:45 — How AI changes creative work: prompting, iteration, and removing human middlemen 31:04 — Personalized marketing, emotional targeting, and the future of one-to-one persuasion 33:54 — AGI, recursive intelligence, and why the sci-fi future feels uncomfortably close 36:03 — What humans are still "needed" for when work gets automated 39:25 — AI, time freedom, and the trap of using saved time to just do more work 40:09 — Eisenhower matrices, family priorities, and deciding what actually matters 41:24 — What Chris is best at: persuasion, performance, and reading the room 43:08 — When persuasion backfires: scope creep, people pleasing, and values drift 47:39 — Chris's AI book experiments and what machine "thought" reveals about human anxiety 53:16 — Delta Digital Agency, how Chris works, and where to follow him online