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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 businesses, especially as the macro-economy crumbles Things we're doing different this time around How to set up operations to run multiple businesses and why it's important to separate all revenue and accounting accounts Relay Finance Wave Ramp card since Brex isn't working with non-VC anymore Why we're building Hire with Grit, a headhunting business out of the Philippines Getting our first few deals under our belt and figuring out our lane Building Docsfresh and why we're starting on Intercom Why working on multiple things gives you energy and learnings you can't get through one business Starting sponsorships for the pod Landon starts continuous glucose monitoring with Levels Snapchat drone cam: Pixie

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 schedule with kids How they scale support with 60k users Finding talent overseas (ie. Hire with Grit) Bootstrapping vs funding 

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.to How did you meet all of the high profile angel investors that joined your seed round? Operators as investors The current funding market with valuations dropping What were the first things Daniel spent the money on? Pivoting Arrows to an integration-based product (currently focusing on Hubspot) Narrowing focus for the product and how that allows you to improve your marketing content Marketing assets: Templates and guides (Arrows guide to customer onboarding on Hubspot)

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" How are you finding great people to hire remotely? Quantifying success by time spent in the product vs. revenue (early on) What are the weirdest use cases you've seen with Punchlist users? How do you sell to agencies? Paying over $20k for the .com and why it's a no-brainer

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 cashflow entities? If you buy a SaaS what's the optimal length of time before you sell it? Hard to maintain the tech/security overtime Platform risk on things like Intercom or Shopify  Links: Hillchart.app (Hillcharts for Notion, Clickup, Github, Trello, Gitlab) Intercom <> Jira App Highways.io (Intercom integration for A bunch of CRM apps)

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)? Startup valuations declining alongside public tech company valuations What does this mean for companies that raised at crazy valuations over the past two years? Will they all die? Why Kyle is a weirdo for not watching the Super Bowl

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 momentum

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.

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 Building vs. buying Landon reviews his fancy new espresso machine (and Kyle confuses semi-automatic with Semisonic) Links & Resources: MicroAcquire Terra Kaffe Nespresso Bottomless Coffee (← Kyle's referral link) Trade Coffee

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 building businesses Doubling down vs. autopilot vs. freedom to build other stuff Thinking critically about the end goal to maintain optionality How much is "enough"? How do we build an asset that affords our team a comfortable life + enables us the freedom to work on anything we want to work on Profit-sharing as a simple, shared incentive structure Acknowledging the moment: the difficult and tragic end of the 20-year American occupation of Afghanistan Where do these events fall in the arc of history? (local vs. global optima) Podcast chats as historical markers Links & Resources: fatFIRE subreddit (Wealth and Financial Independence/Retire Early) MwG episode 36 with Tyler Williams of Motion Array Income vs. Happiness curve Local vs. global optima

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 Experimenting with founder-friendly funding options Micro-acquisitions and the surrounding ecosystem Landon's list of ideas (featuring "something for AWS" 🤣) Exploring new businesses (within constraints) Links & Resources: MicroAcquire Userfeed

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 that point to templates accessed by filling out an email form Hubspot form Links: Workshop Workshop Raises $3mm Previous episode with Derek @dhomann

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's brought on $100k in ARR in the past few months How to find these opportunities How we're feeling about the Userfeed acquisition six months later  Outbound sales email Copy pointers Industry-based sequences Tactics When email works and when it doesn't How we approached outbound at Rigor (selling to enterprise in a highly competitive incumbent market) Personalization do's and don'ts Why making assumptions in emails work Landon's first seed investment (Grayscale). See episode 15 where we talked to the CEO of Grayscale (Ty) about his business. By the way, they're hiring. Links: MixMax Hubspot Rigor  

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 important

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 Links & Resources: Clubhouse (no, not this Clubhouse) Capiche.fm - Talk to the internet Uncle Nearest Whiskey Agora - Realtime video and voice engagement New Ad Reform website on Webflow Endorsal - Customer testimonials, automated Checkly - Delightful active monitoring for developers Mainstreet Taxfyle Coco Floss Bottomless Coffee (Kyle's referral link)

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 bootstrapped businesses need to find free/cheap distribution channels Venture Studio model  Failure.inc Some ideas he's cooking up for his next venture Links & Resources: Motion Array Artlist acquisition of Motion Array Failure.inc Tyler Williams on Twitter

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 design in the works Regulation changes for crowdfunding   Links & Resources: Pipe Haus MiniMeis Casper glow lights Exposure Coco Floss Fatherly

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  Learnings are helpful Leads to more competitors More interested in klout instead of business Spending more time showing you're building in public than actually building Many 'open startups' move away from that as they grow Giving a business more time to mature 90% of companies still aren't using cloud-based software These are the unsexy niches Links & Resources: Salesforce, Slack, and the future of work Bump