Sponsored by Fetch Truck Rental. Truck rental made easy. To learn more about AdLib. Twitter: @HauptmanMichael Remote workspaces Recent business woes Media Math as AdReforms first customer Mike's connection to MediaMath What happened when MediaMath went down Recovery, options Repercussions Possible next steps Ways to stay in the game Gaining and kee…

Sponsored by Fetch Truck Rental. Goal: precipitate the repeal of 174 changes But how? Get 1,000+ signatures on the Small Software Business Coalition Letter to Congress by April 10th Sign the letter → Small Software Business Owners AllianceSD Michele’s Twitter: @mjwhansen Michele’s latest Twitter thread about Section 174 changes…

Sponsored by Fetch Truck Rental. Truck rental made easy. Big Band Software how you run multiple businesses and hiring How do you structure this from an entity standpoint What can founders do to prepare for sale What metrics, P&L line items matter SaaS acquisition market during these tougher times Niches that are doing well Sect 174…

Personal updates Retreats and Conferences, Kyle at Big Snow, Tiny Conference Kicking off 2023 and the year ahead Exploring adjacent use case and tailoring products to new needs Podcast repurposing Tip of the week - high yield savings ratesLandon Bennett, Kyle Conarro

Beer vs. Wine vs. Mixed Drinks, all good. Camo and OSX iPhone WebCam App, don’t get a fancy webcam, just use your iPhone TypeDream.com website builder Thnks.com gifting for business Claap.io video clip / screen sharing and feedback app TLDV.io Recast.studio Museapp.com - open canvas, white board type idea building, planning, collaboration platform …

https://www.sendspark.com/ Bethany breaks down Sendspark The problem of stale content in help center Bethany discusses integration into Intercom Bethany explains origins of Sendspark, was in marketing at another company when she and co-founder realized the need Bethany as a Userfeed customer Fundraising for Sendspark, product usage metrics and acti…

Sponsored by Punchlist: Close the loop on creative feedback and get your projects done. Sign up at punchlist.com and use the promo code GRIT for your first month FREE of Punchlist Team (or 10% off any monthly plan) --- Notes: Helping people sell more things is the right place to be Taplio: 6-figure ARR Tweethunter: 7-figure ARR Why build two separa…

Sponsored by Punchlist: Close the loop on creative feedback and get your projects done. Sign up at punchlist.com and use the promo code GRIT for your first month FREE of Punchlist Team (or 10% off any monthly plan) --- Notes: Growing our candidate pipeline for Hire with Grit What we look for in candidate interviews Video setups Energy/enthusiasm Ma…

Episode Notes Sponsored by Punchlist: Close the loop on creative feedback and get your projects done. Sign up at punchlist.com and use the promo code GRIT for your first month FREE of Punchlist Team (or 10% off any monthly plan) --- Notes: Our first solo pod. Weird? We're also on YouTube now! Weirder? 😜 Hire with Grit update Already placing folks a…

Sponsored by Punchlist: Close the loop on creative feedback and get your projects done. Sign up at punchlist.com and use the promo code GRIT for your first month FREE of Punchlist Team (or 10% off any monthly plan) --- Notes: Starting multiple new ventures Zeromile.io HirewithGrit.com Zeromile.io#docsfresh Hillchart.app Why are we starting more bus…

Links Bonjoro.com Matt Barnett Notes Landon tells Matt about his funny Bonjoro story Landon talks about Docs Fresh, a new Intercom app their about to launch How Matt stair-stepped to Bonjoro through a video insights agency SaaS Virality (Bonjoro videos) How they've grown to multiple millions in revenue without an outbound sales team Workday schedul…

Notes: Daniel Zarick (Founder of Arrows.to) Why it's hard to do a podcast about your business when you're growing a company in a competitive category Learning about the compounding of SaaS with Daniel's Twilio experience (23rd employee) Some markets are a lot bigger than you think Daniel talks about going from bootstrapper to VC-funded with Arrows.…

Links Punchlist.com: Close the loop on creative feedback and get your projects done Techstars Atlanta Overline VC Notes Why raise money vs. continuing to bootstrap? How to get the most out of an accelerator? What were the most interesting startups to come out of Techstars? How to find a co-founder? How did you raise $2mm? "Team, team, team, product…

Notes: What it was like to start our business (the hard times) Building out our new home offices A new product: recurring website screenshots Building landing pages before building the product How important is SEO Userfeed/Bump being sold again for a big return in only one year from the initial sale Are SaaS businesses being flipped or used as cash…

Notes/Links Ad Reform's first sales without the founders! How soon should a company hire a sales rep? Is the product management role shrinking in a remote-first world? Peter Levels tweet Profit-first as a service Matt Wensing tweet Is Facebook crumbling? And is that going to kill small businesses that rely on that growth channel (e.g. DTC brands)? …

Notes Typefully: Twitter threads & analytics Matter: a better reader Calendly Twitter drama Stripe/YC mob drama Marvel: productized content service Purchasing a $1k course Project work vs. sales work and the feeling of momentumKyle Conarro

Kyle and Landon discuss 2022 planning, talking to as many prospects as possible in the early days, why some entrepreneurs are afraid of rejection, the wave of competition in SaaS, and the different levels of authentic demand.Kyle Conarro

Back after a lengthy break, Landon and Kyle discuss Atlanta sports (and the World Series champs), collections, valuations & more. Today’s Topics: The Atlanta Braves are World Series champs!? Iterating on and improving new hire onboarding Bookkeeping mania: adding granularity, cleaning things up Micro-acquisitions, Micro PE, and wild valuations Buil…

In part two of the conversation, Landon and Kyle discuss experimenting with approaches to building businesses, how much is "enough", and reward and incentive structures as companies grow. They also touch on the current moment: the end of the 20-year American occupation of Afghanistan. Today’s Topics: Experimenting with new markets and approaches to…

Landon and Kyle chat about parenting, productivity, and new business ideas. Today's Topics: A new Ad Reformer! Landon had a baby boy 👶 Parenting through a pandemic What could (and would) you do with more time? Deliberately setting aside time for thinking & strategy Productivity, output, efficiency, and leverage The luxury of owning your schedule Ex…

After bootstrapping Median, why go venture-backed with Workshop? Derek talks about their $3mm seed Easier to raise after some wins What has been different about having capital from the start? Derek talks about some of the marketing strategies that are helping them build up a large following in the HR space Acquired a newsletter for $6k Running ads …

Notes: First post-covid vacations New hire running customer operations and freeing Landon up to sell The struggles of handing-off tasks you've owned for years Force testing how the business runs without you What is a customer ops manager? What Landon has been doing on the outbound sales side and how it's going A new product direction/use case that'…

Landon and Kyle discuss growth, hiring, and selling business ideas. Today's Topics: Getting back in the office Growing revenue by following leads, expanding offerings Hiring for help with customer operations Differentiation vectors: usability, functionality, design, etc. A storefront for business ideas? Coming soon: Made with Grit swag…

Notes: Why did we sell? How did we sell the business? MicroAcquire Managing leads and sharing information with potential buyers How long did it take? What were the terms? What went well and what would we do differently? Why focus is importantKyle Conarro

Today's Topics: Clubhouse takes...what is it good for? Update on Landon's stock trading "hobby" What we're drinking New Webflow marketing site launched It's tax time - R&D tax credits & filing services Update on what we're buying: Cocofloss, coffee delivery Landon got a new Apple watch Changing the default music app on iOS We're getting M1 Macbooks…

Episode Summary Tyler Williams on bootstrapping and selling Motion Array for $65 Million. Episode Notes Today's Topics: After selling your company for $65mm what was your first purchase? The story on how they sold the business Why they bootstrapped the business What is Motion Array and how did Tyler come up with the idea What move really made the b…

Today's Topics: A lot of momentum for alt-funding options like Pipe Money is cheaper, with less "baggage" than ever before Marketplace for selling a smaller SaaS is growing Best time ever to be a bootstrapped founder Comparing our march to $1mm ARR vs what it was like getting there in our previous company 5 years ago What we're drinking Recent fanc…

Today's Topics: Deleting Twitter from phone and using Mailbrew What are we drinking How we performed our first profit share Why invoice collections are a huge pain for a small team Bootstrapped business ideas Made with Grit t-shirts Links & Resources: Mailbrew Tip Top canned cocktails Nathan Barry: Profit-sharing for bootstrappers…

Landon and Kyle discuss the idea of avoiding popular SaaS markets and give their thoughts on building in public (while sipping on some bourbon & eggnog). They also give their thoughts on some of the recent SaaS acquisitions. Today's Topics Include: Their podcast drinks of choice Acquisitions of Kustomer (Facebook) & Slack (Salesforce) New product: …

Landon and Kyle discuss their business bouncing back from the dip they experienced during the beginning of the pandemic. They also discuss their previous company getting acquired by Splunk. Today's Topics Include: Kyle's long absence from the podcast Ad Reform's revenue bouncing back strong after the pandemic dip Userfeed launch of a new Intercom a…

Landon and TJ discuss what it's like transitioning from services to products, bootstrapping, selling to NGOs/healthcare, and being motivated by the impact their products have on the world. TJ also talks about how his global health data SaaS is having quite a moment in the year of COVID, sparked by a free tool that tracks Coronavirus data. Today’s T…

Landon and Baird discuss what it's like starting and running multiple SaaS businesses. Baird's businesses include Wavve, Zubtitles, Duplikit, and Churnkey and are doing over $2mm ARR combined. Today’s Topics: Should you build more than one SaaS? One company or multiple? Dealing with support/churn across multiple businesses What's more important: gr…

Jeff Gardner of Graphy joins Landon and Kyle to discuss his 8-year journey at Intercom. He chats about the early days of the product (he was employee #4), growing a support team from 1 to 100, launching a developer platform, and more. Today’s Topics: Intercom pricing (and potential IPO?) Growing support in lockstep with customer growth The evolutio…

Landon chats with Derek Homann, co-founder of Median and Workshop, about bootstrapping, working on multiple SaaS products, taking money off the table, and more. Today’s Topics: Building SaaS outside Silicon Valley (in Omaha, in Derek's case) Running multiple SaaS products as a small, bootstrapped team Derek's career journey: technical recruiter > c…

Kyle and Landon share a company update, then chat about the Facebook ad boycott, stocks, and HEY. Today’s Topics: How the pandemic has impacted revenue and growth Paused customers are returning...will that continue? The pain of getting a home loan as a bootstrapper The Facebook ad boycott: meaningful, or just posturing? Investing a little money for…

Kyle and Landon discuss recent changes to their product development and marketing processes. Today’s Topics: The psychological impact of slow growth Objective improvements vs. psychological tricks Balancing commitment and responsiveness Prioritization and execution: Serial process, or concurrent threads? Shipping cadence: Minimizing work-in-progres…

Kyle chats with Andy O'Hara, a finance guy turned healthcare entrepreneur (and now a self-taught developer). Listen as they discuss Andy's experience growing an on-demand pediatrics business. Today’s Topics: The acquisition of Andy’s recent company Learning to code on the job at Chiron Health Building an app simply for an easier dev - and user - ex…

Landon chats with Brandon Cummings about his journey from finance, to tech, to starting a non-profit in Atlanta that feeds 6,000 people per week. Today’s Topics: Brandon’s journey from finance, to biz dev, to engineering The demise of Voxa Bootstrapped vs “going big” A detour into data science Going full-time on a side project Taking a new job afte…

Landon & Kyle have a heated discussion about B2B customer support. Today’s Topics: We got the PPP loan! Decided not to run for president What we’ve learned about B2B SaaS support Stop calling them support “tickets” Live chat isn’t the problem Choosing to be opinionated about customer feedback management Don’t make your customers do all the work Why…

Today’s Topics: Kept up all night by…the dog What we’re working on New podcast idea Handling subscription pause requests due to COVID-19 Automating payroll Virtual coffee with the founder of a new SaaS Looking back at the inflection points for Ad Reform Trying to monetize free software What we would have done differently if we started the business …

Kyle ventures back to the office to water the plants, Landon has been researching note-taking apps, and the governor of Georgia is reopening bowling alleys. Today’s Topics: An update on the COVID-19 life and distant socializing Georgia ignoring the stats to reopen gyms, restaurants, massage parlors Bowling alley conspiracies Note taking apps for th…

Landon and Kyle talk about the strategies and (many, many) tools they use (and have tried out) to collaborate remotely on work. Today’s Topics: COVID-19 drinking game (the new normal) All we can do is keep moving forward Blood-sucking sales reps How our team collaborates remotely from all over the world Using Slack only for what it's good for Our a…

Kyle and Landon reflect on how fast things have changed, how COVID-19 has affected the team so far, and how running the companies conservatively has ultimately paid off. Today’s Topics: A break from podcasting because of "you know what" The emotional phases of a pandemic How our remote team has been affected Building a no-code app to keep track of …

Landon and Kyle talk about the struggles of hiring a remote international team while still building a product and moving bigger deals forward. Today’s Topics: Kyle and Landon chat about what they’ve been doing lately Challenges that come with hiring remote international staff Discovering unnoticed fees when paying internationally with Bank of Ameri…

Kyle talks to Pete Bernardo about leaving agency life and starting Punchlist Today’s Topics: Our second guest Pete Bernardo What is Punchlist The problem that Punchlist is solving for agencies and businesses Naming Punchlist Starting as a solo-founder and bring people in later Past businesses & co-founder fallouts Rolling out new pricing through in…

It’s that time of year again: Tax season. Landon & Kyle talk about what they’ve learned (or haven't) about accounting for startups over the years. Today’s Topics: Doing the boring stuff (taxes, bookkeeping, booking flights, etc.) Stuff you should leave until you’re actually making money Got ourselves a bookkeeper Using a product-ized service for fi…

Landon sits down with Ty Abernethy, Co-Founder and CEO of Grayscale to discuss getting to $60K ARR with an MVP, getting blacklisted for sending too many outbound sales emails, and VC vs Bootstrapping. Today’s Topics: How Landon and Ty met at a strangely-named entreprenuer meetup Grayscale’s 30-second elevator pitch Accidentally naming Ty’s company …

Landon and Kyle discuss the hard questions they've had to ask about the fate of Userfeed. As well as the conclusion they've finally come to. Today’s Topics: Struggle to run two businesses without neglecting one Weighing the options for Userfeed The decision we’ve landed on What’s next The loss of a hero Links & Resources: Basecamp Wildbit…

Landon and Kyle prepare for an Atlanta Hawks game while chatting about dev emergencies, content marketing, and tricks for LinkedIn outreach. Today’s Topics: Our first remote episode! A small emergency on the engineering side Even accountants don’t like accounting Using StoryChief for content marketing using keyword research and SEO Repurposing blog…

As Ad Reform continues to grow, Kyle and Landon talk about the tools and tactics they are using to stay focused on the priorities. Today’s Topics: Our most popular episode yet We’re killing it! Or so it seems? Can’t get back into a groove after the holidays Learning to balance a growing list of priorities Tools for staying productive When should th…