Made with Grit

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 business take off The importance of SEO and why bo...

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 fancy DTC purchases we've made Made with Grit T-shirt...

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: Bump Building in public? Pros and cons  Learning...

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 app: Bump Kyle and Landon's previous employer, Ri...

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 Topics: ATL ties Bootstrap or raise? Services to p...

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: growth or retention? Moneyball approach to prioritiz...

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 evolution of hiring needs as a company scales Being remote...

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 > customer support > director > founder Latest projec...

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 fun (and maybe profit) HEY, Basecamp, and DHH's T...

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-progress, maximizing throughput Marketing: one-month-at-a...

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 - experience Andy’s journey building a telemedicine bu...

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 after COVID-19 shuts down the business Building an ope...

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 you should be collecting customer feedback from t...

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 today Iterative billing strategies Joe Rogan and U...

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 the iPad Ad Reform’s cash situation and the hot new...

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 async-first workflow and why it's better than the 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 COVID-19 cases where our different team members li...

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 America R&D tax credit Feeling overwhelmed when day to...

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-person conversations to get feedback The technica...

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 filing taxes Another benefit to being apart of an in...

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 after a disease Coming up with the initial idea Ge...

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 posts Should we use Webflow? How we do LinkedIn o...

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 the founders stop providing full-time support? Links...