meta_pixel
Tapesearch Logo
Log in
Startups For the Rest of Us

Episode 562 | "Measure Twice, Cut Once" + SaaS Holy Grails (A Rob Solo Adventure)

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9819 Ratings

🗓️ 10 August 2021

⏱️ 20 minutes

🧾️ Download transcript

Summary

In Episode 562, join Rob Walling for another solo adventure to talk about enterprise sales, mental frameworks for founders, undoable decisions, and how to handle being approached about an acquisition. The topics we cover [2:33] Enterprise sales advice [5:48] Measure twice, cut once for SaaS [10:56] Holy Grail of SaaS: Expansion Revenue [13:12] Holy Grail of SaaS: Virality [14:25] Holy Grail of SaaS: Big space with slow-moving incumbents [15:46] Things to keep in mind when being approached about an acquisition Links from the show Josh Ledgard on Twitter Rob Walling (@robwalling) | Twitter If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify | Stitcher

Transcript

Click on a timestamp to play from that location

0:00.0

Right, if you've raised half a million dollars and you're making decisions about $1,000 here, $5,000 there, you are able to throw that money around and basically move faster.

0:10.6

And you don't get the decision fatigue or kind of the nitpick fatigue that you get when you are truly bootstrapping.

0:20.1

This is sort of for the rest of us.

0:21.6

I'm your host, Rob Walling.

0:22.6

For more than 10 years on this show, we've covered topics relating to building and growing

0:27.6

startups using an ambitious but a sustainable approach.

0:30.6

We're not willing to sacrifice our health or our relationships to grow a company.

0:34.6

We want to build real businesses with real customers who pay us

0:38.2

real money. Welcome back to the show. Thanks so much for joining me. This week, it's a Rob Solo

0:42.2

Adventure. I'm going to be diving into a couple things that I found on Twitter. It's actually a

0:46.5

tweet that I sent out a couple weeks ago, as well as a really interesting thread on

0:50.1

enterprise sales from Josh Ledgard of Kickoff Labs and talk about a couple other

0:55.5

mental frameworks and things that have been on my mind recently. As I've said before,

0:59.9

a lot of these topics that I talk about in these solo adventures, 10 years ago would have been

1:04.5

a blog post or a chapter of a book. And these days, given everything that I have going on with

1:09.1

MicroConf and Tiny Seed in this podcast,

1:11.8

I don't have as much time to write as I would like, but I'm still exposed to so many new

1:16.7

ideas on a weekly basis as I look across 60 companies that I'm invested in. A chunk of those

1:23.1

are through Tiny Seed and a chunk are private angel investments that I made before starting Tiny Seed.

1:29.2

And I'm seeing a lot of patterns. And I'm talking to a lot of founders who are facing things like

1:33.3

massive growth or not enough growth or planning for an exit or getting an offer or considering

1:40.8

selling and wondering what they might sell for, having to fire an employee,

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Rob Walling, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Rob Walling and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.