Landon Bennett & Kyle Conarro

Made with Grit

A show about bootstrapping SaaS businesses. Hosted by Landon Bennett and Kyle Conarro, co-founders of Zeromile.io.

Author

Landon Bennett & Kyle Conarro

Category

Technology

Podcast website

listen.madewithgrit.fm

Latest episode

Jul 25, 2023

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Episodes

60 : Mike Hauptman - When the platform you're built on goes bankrupt overnight 25.07.2023

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 keeping Momentum

59: Section 174 with Michele Hansen 30.03.2023

 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 Alliance SD Michele’s Twitter: @mjwhansen Michele’s latest Twitter thread about Section 174 changes

58 : Chris Reedy, Big Band Software 28.03.2023

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

57 : The Year So Far and Looking Ahead 21.02.2023

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 rates

56 : A few of our favorite (software) things 13.12.2022

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 Felt.com - MAPS! Swarmia.com - Engineering organiz...

55 : Landon Chats with Bethany Stachenfeld of Sendspark 14.10.2022

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 activation Initial product Dev strategies, funding and...

54: Building a 7 & 6-figure SaaS at the same time with Tom Jacquesson of Tweethunter and Taplio 04.10.2022

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 separate products when they could potentially be...

53: Figuring out how to grow our hiring business 11.09.2022

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  Marketing experiments for the podcasts  Repurp...

52: Landon's first solo update on the new businesses 12.08.2022

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 and seeing some good demand from non-friendly...

51: Starting a couple of new businesses 27.07.2022

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 crum...

Building a fast-growing video-based SaaS (with Matt Barnett, founder at Bonjoro) 30.06.2022

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...

Size of markets, pivots, and funding with Daniel Zarick (founder of Arrows.to) 11.05.2022

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...

From bootstrapped solopreneur to raising $2mm with Pete Bernardo of Punchlist 08.04.2022

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 remotel...

47: Our ex-SaaS is being sold...again! 24.03.2022

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 optima...

46: Sales are officially delegated and we try a new podcast format 28.02.2022

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...

45: Upping our content game & tech Twitter drama 10.02.2022

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

44: Planning for 2022, competition in SaaS, and authentic demand 27.01.2022

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.

43: The curse is broken 25.11.2021

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 espre...

42.5: Parenting, productivity, & starting more businesses (part 2) 31.08.2021

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 v...

42: Parenting, productivity, & starting more businesses (part 1) 25.08.2021

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...

41: From bootstrapped to venture-funded w/ Derek Homann 17.06.2021

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...

40: A new hire, outbound sales and finding new use cases for your product 09.06.2021

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...

39: Want to buy our business ideas? 29.04.2021

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

38: We sold one of our businesses 16.04.2021

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

37: Who has time for Clubhouse? 26.02.2021

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 Clubho...

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