Smart Bear Live

Jason Cohen

The show where a startup founder takes the hot seat, opens up their business, and explains their biggest challenge. Then we dig in: a few other founders who have already solved that challenge in their own businesses. This is not an interview. There's no script. This is the messy, uncomfortable process of solving a real puzzle faced by a real company. No ads, no affiliate links, no heavy editing, no follow-on courses or consulting. We're doing this for each other and for the love the game. It's a workshop, but also it's therapy. For founders, what's the difference?

  1. 3 days ago

    E13 w/ Ruben Gamez: How to Restart Growth in a Stagnant SaaS Business

    Michael Koper says Nusii, his proposal software, is simpler than its rivals, but every one of those rivals say that too. Revenue has been flat for a few years now at around $10k per month.How does he stand out? Buyers do indeed want “simple,” but what else?Cohost Ruben Gamez and I dig in: A candid working session including:- Ruben dislikes attention, until it brings paid upgrades- agencies stay with Nusii, but too few sign up- are missions only interesting to big customers?- Nusii’s homepage says “serious” but also “simple”- the loyal, paying customer who’s still a lossME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING MICHAEL KOPERFounder of NusiiTwitter | LinkedIn WITH COHOST RUBEN GAMEZFounder of eSign software SignWell and proposal app Bidsketch.SignWellBidsketchTwitter | LinkedIn TIMESTAMPS (00:00) - Proposal software stuck at $10k a month (02:09) - Homepage headline: why "serious" misses (07:56) - Why proposal software wins more deals (13:59) - Table-stakes features vs. being simplest (21:18) - Everyone claims simple: compete with Word (29:21) - Don't go horizontal in a crowded market (33:34) - Commodity products need a real vertical (39:00) - Marketing when it's not your strength (42:43) - Narrowing down the target customer (46:34) - Conferences: when they're worth the trip (52:46) - A mission: help customers win deals (01:00:15) - Finding a mission later, like WP Engine (01:06:02) - Standing out still needs 10x the leads

    E13 w/ Ruben Gamez: How to Restart Growth in a Stagnant SaaS Business
  2. 1 Nov

    E12 w/ Tibo Maker: How can a $40K MRR SaaS be losing 20% of Its Customers

    20% of Post Bridge's customers leave every month -- massive churn that puts a hard ceiling on growth. Jack Friks’s tool sends posts to many social platforms from one dashboard, and he built it in public on X, where his personality attracted other builders, but not the business marketers he needs. How does he choose the customer to build for? Asked what Post Bridge does best, he says, “I don’t know.” Cohost Tibo Louis-Lucas and I dig in: A candid working session including:- Tibo's one-price fix: $1 per account, minimum 30- why an A/B test won't tell you your ICP- is LinkedIn where his real buyers are?- how narrowing the ICP expands sales, but it never feels like it- be himself online, or change for his customer?- users with 15+ accounts expect to pay $500, not 50 ME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JACK FRIKSCurious guy who likes creating things and loves his wifewebsitepost bridgeTwitter WITH COHOST TIBO LOUIS-LUCASBootstrapped SaaS founder. Sold Tweet Hunter and Taplio to lempire in 2022 ($10m), now building Revid, Outrank, Squad, Bazzly, PostSyncer and SuperX (yeah that’s a lot 😅)Newsletter (80k+ founders) & portfolioRevid, AI videoOutrank, SEO on autopilotBazzly, acquisition on RedditSquad, AI teammates for workSuperX, grow on XTwitter | LinkedIn TIMESTAMPS (00:00) - Doubling Post Bridge despite 20% churn (04:26) - Make AI plugin signups stick (09:41) - Growth spurts, and being best at one thing (13:18) - Features you wouldn't hand to an LLM (18:20) - 20% churn and three kinds of cancels (28:06) - Fix churn at the top of the funnel (35:40) - Channel-founder fit vs. the ICP (39:51) - Defining an ICP that actually exists (45:00) - Why LinkedIn may be the best channel (49:21) - Stay yourself, but know your audience (53:58) - Which churn is worth fixing (56:25) - Is $100k MRR the real goal? (59:12) - Pricing: why fewer choices convert (01:02:40) - Who each pricing tier is for (01:05:45) - Anchor tiers and $1-per-account pricing (01:09:30) - How Tibo and Jason would grow it (01:15:40) - Why choosing a customer feels so hard

    E12 w/ Tibo Maker: How can a $40K MRR SaaS be losing 20% of Its Customers
  3. 24 Oct

    E11 w/ Mariya Delano: How to Fix a SaaS Trial-to-Paid Conversion Problem

    About half of Userlist’s paying customers never fully set up the email automation they paid for. Jane Portman and Benedikt Deicke built Userlist over nine years for sophisticated SaaS marketers, but its onboarding is free and optional.How do they get customers to do the setup that makes the product valuable and sticky? Making onboarding mandatory, and charging for it, could scare off the very customers they want most. Cohost Mariya Delano and I dig in: A candid working session including:- an onboarding fee that “needs to hurt”- a one-person business that spent $20k on consulting- when a low price looks “suspicious” to buyers- a cofounder admits she can’t do enterprise sales- the $149 tier Jane says should be eliminated- they can’t name one podcast their buyers hear ME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JANE PORTMAN & BENEDIKT DEICKEUserlistJane’s UI Breakfast podcastTwitter | LinkedInBenedikt’s Slow & Steady podcastTwitter | LinkedIn WITH COHOST MARIYA DELANOKalyna MarketingThe Marketing Speakeasy podcastADMD newsletterLinkedIn REFERENCED IN THIS EPISODETinySeedMicroConfSegment“Marketing Technology Landscape”—chiefmartec TIMESTAMPS (00:00) - Userlist's stalled growth: who is it for? (03:53) - Why growing customers cancel (09:10) - Email ROI is measurable: wrong customers? (12:51) - Lost champion: spread value beyond one user (20:09) - Fixing onboarding: HubSpot's forced training (24:14) - A $10K implementation fee for onboarding (31:34) - Selling to bigger budgets: the $20K client (36:29) - Priced below Mailchimp and ConvertKit (44:00) - Where are the customers for geeky features? (48:25) - Should Userlist go simple and down market? (53:52) - Do thousands of geeky marketers exist? (57:40) - Next steps: interviews and $20K onboarding (01:03:00) - Be proud of the path that got you here (01:07:11) - Imposter syndrome and perfectionism

    E11 w/ Mariya Delano: How to Fix a SaaS Trial-to-Paid Conversion Problem
  4. 18 Oct

    E10 w/ Jessica Malnik: Plateaued at six figures, but still hungry

    Brett Lindenberg’s startup Mindstamp puts six figures of profit in his pocket every year, helping businesses create interactive videos for training and sales. But growth has leveled off, and he’s having trouble changing that.Does he niche down to one kind of customer, or stay general and change how he reaches the market? Either way, most of the buyers he wants have never heard of interactive video. Cohost Jessica Malnik and I dig in: A candid working session including:- the cheaper plan that has him fishing in bad waters- why his best buyers aren’t searching for him- SOC 2, and why Mindstamp should never issue the certificate- certifications people care about at the identity level- teaching better interactive video as the marketing =================ME ME ME!!!=================Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn =============================STARRING BRETT LINDENBERG=============================MindstampTwitter | LinkedIn ==================================WITH COHOST JESSICA MALNIK==================================HomepageSubscribe on NewsletterSubscribe on YouTubeThe Remote Work TribeTwitter | LinkedIn ================================REFERENCED IN THIS EPISODE================================“The Iterative-Hypothesis customer development method”“Not Business Advice” books—Alex West TIMESTAMPS (00:00) - Plateaued SaaS: niche down or stay general? (04:11) - Too general, or just customizable? (08:21) - Who sticks? Medical continuing education (13:05) - A cheaper plan is fishing in bad waters (17:38) - Where do your best customers go? (22:25) - Nobody knows interactive video exists (27:20) - Making videos for customers as a service (34:21) - Certification partners: the SOC 2 case (45:38) - Win certifiers who want to stand out (54:18) - Content marketing: teach better videos (01:00:25) - 90-day plan: interview your customers (01:04:47) - Box-tickers vs. buyers who really care (01:07:15) - Energized, with hypotheses to test

    E10 w/ Jessica Malnik: Plateaued at six figures, but still hungry
  5. 4 Oct

    E09 w/ Jon Sturgeon: AI changed his agency's model. Should he grow or sell?

    Mario Peshev reduced his agency from 60 to 30 employees thanks to his own AI innovations. But almost nobody there is working on landing new clients.Pouring money into sales means building a machine he has never had. He could sell, but then he has to prove that this agency is worth a lot of money. Cohost Jon Sturgeon and I dig in: A candid working session including:- agencies in the world of AI- why an NPS of 90 proves nothing- bench time: waste, or a feature clients pay for?- a live cold-call role-play ===============ME ME ME!!!===============Subscribe on YouTube📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn ==========================STARRING MARIO PESHEV==========================DevriXPersonal siteNewsletterTwitter | LinkedIn ================================WITH COHOST JON STURGEON================================Dingus & Zazzyuhoh.com (an IT company for businesses that don’t have IT problems)NewsletterTwitter | LinkedIn ===============================REFERENCED IN THIS EPISODE===============================“The Effortless Experience”—Dixon, Toman & DeLisiHypergen, cold email TIMESTAMPS (00:00) - Can AI-run agencies survive the next five years (02:21) - Eighteen years building DevriX to a crossroads (07:10) - The walk-away number game (10:01) - Why productizing DevriX would be a mistake (18:23) - One and a half salespeople for a 35-person agency (30:45) - Why an NPS of 90 proves nothing (36:50) - Agencies in the age of AI: adapt or die (50:45) - Bench time: waste or a feature clients pay for (01:01:25) - Rebuilding go-to-market from scratch (01:24:22) - Live cold-call role-play (01:28:40) - Is a 6 million dollar exit even realistic (01:40:34) - EBITDA multiples and the AI-narrative buyer (01:44:35) - The real path forward: spin off, sell, or stay

    E09 w/ Jon Sturgeon: AI changed his agency's model. Should he grow or sell?
  6. 27 Sept

    E08: Creating customer interview questions before you have customers

    He built it, and they didn't come.Rison Simon built PainPointy to scan Reddit so that marketers could learn the pain points of their customers and come up with article ideas. The problem is he's never had more than six customers. So he has to go interview customers and potential customers, which means first knowing what to ask them. We workshop that with my Iterative Hypothesis method — inventing the questions, then working out which ones are best. ME ME ME!!!Subscribe on YouTube📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING RISON SIMONPainPointyBlogSubstackTwitter | LinkedIn REFERENCED IN THIS EPISODEThe Iterative Hypothesis MethodAI skills that implement the Iterative Hypothesis Method TIMESTAMPS (00:00) - He sold his last startup the week he launched it - this one has almost no customers (02:09) - What PainPointy actually does, and why Rison can't say who wants it (08:37) - The Iterative Hypothesis Method: write down what you think before you ask (14:19) - Why does it have to be B2B? Interrogating your own assumptions (19:08) - The question that doesn't lead the witness (28:33) - Quantity vs quality of leads: the customer who's actually easy to win (39:08) - The real problem isn't a shortage of ideas, it's knowing which one to pick (50:23) - Powers of 10: turning vague guesses into testable numbers (58:11) - Where to actually find people who will talk to you

    E08: Creating customer interview questions before you have customers
  7. 20 Sept

    E07 w/ Dan Martell: 1 big logo won't get him the next 10

    How can George Paladichuk take his startup NaiL from 1 huge customer, to the next 100 customers? Cohost Dan Martell and I dig in: A candid working session including: - finding early adopters in public data- reading job postings to find your buyer's software- the $15K way inside a global franchise- products for many instead of a product for one- should he chase elephants or mid-market? =======================ME ME ME!!!=======================Subscribe on YouTubeGet my bookMy bio + 20 years of articlesTwitter | LinkedIn =======================STARRING GEORGE PALADICHUK=======================NaiLGeorge's siteLinkedInYouTube =======================WITH COHOST DAN MARTELL=======================Dan MartellGrowth Stacking Show (podcast)Martell Method (newsletter)YouTubehttps://twitter.com/danmartell https://ca.linkedin.com/in/dmartell =======================REFERENCED IN THIS EPISODE======================="Buy Back Your Time"—Dan Martell"Crossing the Chasm"—Geoffrey A. Moore TIMESTAMPS (00:00) - Intro: NaiL runs on 90% revenue from one client (01:23) - George introduces NaiL, an AI receptionist for franchise brands (02:58) - Standing out among 800 AI receptionist competitors (04:53) - The real bottleneck: enterprise deals are too slow (08:59) - Why chasing Main Street customers is harder than it looks (12:33) - Money vs speed: mapping enterprise, mid-market, and small business (18:26) - Crossing the chasm: finding customers who already want new tech (23:00) - George commits: doing franchise, not vague "enterprise" (27:02) - The three Fs for spotting early adopters: follow, fund, frequent (35:21) - The holding company angle: land ten brands through one parent (42:59) - Selling a low-cost pilot to get a foothold in new brands (47:41) - Dan's Irving Oil story: the danger of concentration risk (59:12) - Is NaiL a real product, or a bespoke dev shop for one client? (01:04:02) - Dan's homework: partners, conferences, and non-competing locals

    E07 w/ Dan Martell: 1 big logo won't get him the next 10
  8. 13 Sept

    E06 w/ Bryce Adams: Pivoting his strategy into his strengths

    Carl Alexander built Ymir — a serverless AWS platform that deploys WordPress and PHP applications onto a customer's own AWS account — and the twenty-five customers who run production stores on it never leave. They also all pay $39 a month, and nobody new signs up. Did four years falsify the market, or was it the wrong buyers? It's the second one. The $39, the self-serve signup, the WordPress developer he kept aiming at — every piece of the offer points away from the thing he's world-class at, which is teaching people how this works. Cohost Bryce Adams bootstrapped Metorik on the same platform, and he's been telling Carl to charge more for years. He and I dig into who the buyer actually is, and what Carl should be selling him. A candid working session including: - five years of talks, zero customers- $39 versus "bet our company on it"- the joke tier he shouldn't have deleted- what Metorik charged from day one- should he stop going to conferences? ME ME ME!!!Subscribe on YouTube📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING CARL ALEXANDERYmirYmir ReportsBlogTwitter | LinkedIn WITH COHOST BRYCE ADAMSMetorikTwitter REFERENCED IN THIS EPISODE"Using the Needs Stack for Competitive Strategy""SaaSocalypse" video by Jesse Hanley TIMESTAMPS (00:00) - A business customers love but that nobody buys - framing the puzzle, then Carl Alexander and cohost Bryce Adams (Metorik) (04:08) - Diagnosing 4 years of failed WordPress-developer marketing - and proving the market already exists (12:40) - Rejecting the succession-plan fix, then hunting the buyer pattern in Carl's 4 paying customers (17:22) - Engaged developers aren't buyers: why the "resonating" marketing wasn't actually working (22:45) - Finding the real decision-maker: not the developer who claps, the CTO who signs (26:40) - The $39/mo price that contradicts "mission-critical, dependable" (40:10) - "Carl as a service": the $20K consulting offer bundled with $500/mo software (54:29) - Landing on $1,000/mo, validated by Bryce's own Metorik pricing history (59:32) - Redefining the ideal customer: a $5M+ GMV WooCommerce store (01:09:29) - Sell to agencies, not individual stores (01:19:25) - The ICP crystallizes: an agency already committed to AWS that just needs expert help (01:31:25) - The conference rule: only go for leads or credibility (01:37:56) - Carl commits to raise the price before this episode airs (01:40:29) - Closing: the WordCamp party story

    E06 w/ Bryce Adams: Pivoting his strategy into his strengths

About

The show where a startup founder takes the hot seat, opens up their business, and explains their biggest challenge. Then we dig in: a few other founders who have already solved that challenge in their own businesses. This is not an interview. There's no script. This is the messy, uncomfortable process of solving a real puzzle faced by a real company. No ads, no affiliate links, no heavy editing, no follow-on courses or consulting. We're doing this for each other and for the love the game. It's a workshop, but also it's therapy. For founders, what's the difference?

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