Jul 7, 2020 · 46m · startups-for-the-rest-of-us
Episode 504 | 15 Tools We Use to Run Our Business
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In Episode 504 of Startups for the Rest of Us, host Rob Walling and TinySeed Program Manager Tracy Osborne break down the 16 essential software tools powering MicroConf and TinySeed. They share candid assessments of their operational tech stack, providing actionable insights on communication, documentation, marketing, and pipeline automation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Rob holds 63.8% of the talking time here. How this is scored →
Rob as informed peer 5.3 Guest teaching 2.2 Guest disagreement 1.2 Rob pushing back 1.0
speaking balance: gold is Rob, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:19 Tracy's resistance to LastPass adoption
Tracy candidly remarks that she 'died a little bit' when told she had to use LastPass instead of 1Password, pointing out its buggy interface and usability shortcomings.
Hardest push from Rob ▶ 44:27 Rob firmly clarifies Help Scout vs. Zendesk stylingWhen Tracy questions whether Help Scout emails look automated, Rob immediately pushes back to correct her, explaining that she is thinking of Zendesk.
Biggest teaching moment ▶ 36:18 Tracy educates Rob on Twitter's algorithmic feed pollutionTracy lays out why twitter.com has become unusable due to non-follower likes and injected replies, teaching Rob why a third-party client like Tweetbot is essential.
Rob holds their own ▶ 14:58 Rob deconstructs the structural flaws of Notion for writingRob provides a technical, granular critique of why Notion's block-level paragraphs disrupt writer flow and break three decades of standard word-processing keyboard navigation.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Rob as informed peer | Guest teaching | Guest disagreement | Rob pushing back | Why |
|---|---|---|---|---|---|---|
| Baseline Operational Tools: G Suite, Zoom, and Calendly | 5 | 1 | 1 | 1 | Rob outlines foundational operational tools (G Suite, Zoom, Calendly) and explains his rationale for choosing Calendly over bootstrapped options like YouCanBookMe. Tracy playfully chimes in regarding Google's aggressive Meet placement, prompting Rob to vent about unwanted calendar automation defaults. | |
| Team and Community Communication with Slack | 5 | 2 | 1 | 1 | Tracy details managing the MicroConf Connect community on Slack versus forums like Discord or Basecamp. Rob shares his deliberate anti-distraction Slack practices and establishes team norms around synchronous versus asynchronous communication. | |
| Documentation and Collaboration: Notion vs. Google Docs | 6 | 2 | 1 | 1 | Rob outlines the boundary between Notion for permanent documentation and Google Docs/Sheets for collaboration and drafting. He specifically critiques Notion's block-based architecture breaking standard word processing shortcuts, which Tracy validates. | |
| Cloud Storage and Security: Dropbox and LastPass | 5 | 2 | 2 | 1 | Rob justifies choosing Dropbox over Google Drive and LastPass over 1Password due to legacy usage and enterprise switching costs. Tracy admits she 'died a little bit' having to adapt to LastPass given its clunkier UX. | |
| Analytics and Podcasting Infrastructure: Dasharoo, SquadCast, and Castos | 6 | 1 | 0 | 0 | Rob details setting up high-level marketing metrics using Dasharoo alongside squadcast and Castos for podcast infrastructure. Tracy recounts a previous recording nightmare on Zencastr that highlighted SquadCast's superior reliability. | |
| Marketing Automation and Task Tracking: Drip, RightMessage, and Trello | 5 | 2 | 1 | 1 | Rob discusses using Drip and RightMessage for website personalization and Trello for personal task prioritization. Tracy explains her preference for a simpler running Google Doc to-do list, which Rob compares to his historical transition from paper notebooks. | |
| Rapid Web and Content Creation: Squarespace, Voxer, and Keynote | 6 | 3 | 2 | 1 | Rob and Tracy debate the trade-offs of Squarespace constraints versus custom code and WordPress maintenance. Tracy also explains how using Keynote revolutionized their ability to rapidly design and output multi-page PDF guides. | |
| Social Media Optimization: Tweetbot and Buffer | 4 | 4 | 1 | 0 | Tracy explains why third-party tools like Tweetbot and Buffer are necessary to strip away Twitter's algorithmic engagement bloat and batch social posting. Rob acknowledges he was unaware of how bad the default feed noise had gotten and considers switching tools. | |
| Accelerator Pipelines and Support: Submittable, Pipedrive, and Front | 6 | 3 | 2 | 3 | Tracy and Rob discuss their application intake stack using Submittable, Pipedrive, and Front. Rob pushes back to clarify the difference between Help Scout and Zendesk email rendering after Tracy misremembers Help Scout's interface styling. |
Statements from this episode (12)
Rob Walling switched Drip to Zoom for video chat in 2014
“And we use Zoom for video chat and voice chat. And we have for, well, I mean, I used it. We switched to it in 2014, probably with Drip.”
Rob Walling chose Calendly over YouCanBookMe for its Zoom integration
“The only reason that I don't use YouCanBookMe is they didn't have a tight integration with Zoom, where you can click on a link, book a thing, and get a unique Zoom link.”
MicroConf Connect reaches 1,100 community members
“MicroConf Connect with 1100 people who do not work for the same company”
Rob Walling advises using email for non-urgent matters over Slack
“We say, hey, if you don't need to hear back on something for two, 3:04 hours, send an email. And if you need an urgent answer, and you are hung up, and you cannot proceed, or you're on a call, and you're right now, then Slack me, or frankly, send me a text mes…”
Tracy Osborne prefers Google Docs over Notion for real-time collaboration
“Google docs or seeing what people are doing in sheets. It's just so much faster and smoother that I tend to lean to using those tools over notion, even though notion has those things built in.”
Rob Walling finds Notion's block model disrupts long-form writing flow
“And Notion doesn't work that way with long form copy. And I think it's, they make it easier for dragging elements around in a document, but it's a lot harder for me to compose or just straight write and go because my flow is constantly broken by the fact that …”
Rob Walling critiques LastPass usability but notes high switching costs
“Usability is getting better, but it's not great. And then it does have some weird edge case bugs. And since you're not paying that much for it, the support's not great. Like I do have, of all the tools we mentioned so far, LastPass is the one that I'm kind of …”
Tracy Osborne notes TinySeed is actively fundraising for its next fund
“So Tiny Seed, we have people who want to be funded by us, but also, you know, we're fundraising for our next fund.”
Rob Walling prefers WordPress over Squarespace for blogging and podcasting
“I still think WordPress is better for blogging and for podcasting because of the serial nature of it and just how many good plugins it has.”
Tracy Osborne uses Apple Keynote over Adobe InDesign to create eBooks
“To use Keynote to create that multi-page PDF is so much easier and faster than say using something like InDesign. So you can create eBooks really, really fast.”
TinySeed processed 900 initial fund applications using Squarespace, Zapier, and Sheets
“Because our first round of applications was an embedded Squarespace form that went into a Google spreadsheet that pretty soon had 900 rows in it with 30 columns, and then we had to hook into Zapier to send a confirmation.”