Startups For the Rest of Us

Rob welcomes back to the show a frequent guest, Craig Hewitt for a "Where Are They Now?" syle episode. Craig is the founder of Castos and has appeared many times on Startups For the Rest of Us. In this episode, they reconnect and talk about the latest with Castos, from hiring a growth marketer, merging brands, private podcasting, and so much more.

The topics we cover

[3:54] Reflections on hiring a growth marketer 1 year later

[6:92] How did the free trial without asking for a credit card experiment work out?

[8:92] Merging brands and moving into enterprise offers

[19:91] Private podcasting

[23:44] What's new and exciting at Castos

Links from the show

• Episode 466 | Answering Listener Questions With Craig Hewitt
• Episode 493 | A Roundtable Discussion about COVID-19, Working From Home, Payroll Protection and More
• TinySeed Tales - Season 1
• Castos Productions (formerly Podcast Motor)
• Rogue Startups
• The SaaS Podcast Award

If you enjoyed this episode, let us know by clicking the link and sharing what you learned.

Click here to share your number one takeaway from the episode.

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!

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In episode 523, Rob hosts a rapid-fire lightning round of listener questions ranging from whether to focus on one or multiple businesses, finding the right amount of customer research, breaking through slow growth, and teaching entrepreneurship to kids.

The topics we cover

[4:38] If you were starting a business today and you were earlier on in your career, would you try multiple business ideas at once or go all-in on one?

[8:11] If building your first tiny product, like a WordPress plugin, what level of customer research should you do?

[10:56] What advice would you give to someone entering a somewhat competitive market?

[15:55] What questions would you be asking yourself if you had a slow-growing 12k MRR B2B SaaS?

[18:22] How would you go about offloading tier-one customer support?

[20:28] How do you feel about entrepreneurship being taught to children?

[22:24] What are things you noticed that bootstrappers commonly overlooked that are preventing them from achieving their goals?

[23:18] What are some of the biggest takeaways you can see across your portfolio of early-stage SaaS companies?

[25:01] Have you ever built a business that got a fairly large portion of its revenue from services instead of products, but not just you consulting?

[26:56] How do you prepare financially or otherwise for your retirement?

Links from the show

• MicroConf Connect
• SavvyCal
• Stay on Top of Your SaaS Metrics: Know What to Measure to Maintain Sustainable Growth – Craig Hewitt
• The 2020 State of Independent SaaS
• ZenFounder
• Indie Founder Bootcamp
• AudienceOps
• Castos Production (formerly Podcast Motor)

If you enjoyed this episode, let us know by clicking the link and sharing what you learned.

Click here to share your number one takeaway from the episode.

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!

In Episode 546, Rob Walling flies solo for a Q&A episode. With a backlog of great listener questions, Rob discusses qualified small business stock (QSBS), hiring entrepreneurially-minded employees, indie hacking while working at a large company, and more.

The topics we cover

[01:51] Should I switch to a C Corp to take advantage of QSBS in five years?

[05:40] How to attract entrepreneurial employees

[14:19] Indie-hacking while working at a large Fortune 20 company

[19:12] Finding a niche using the Disruptive Innovation

Links from the show

• Episode 442 | Corporate Structures and How the Choice You Make Now Can Impact You Years Down the Line
• Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure)
• The Stair Step Approach to Bootstrapping | Rob Walling - Serial Entrepreneur
• Qualified Small Business Stock (QSBS)

If you enjoyed this episode, let us know by clicking the link and sharing what you learned.

Click here to share your number one takeaway from the episode.

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!

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The topics we cover

• Brian and Scottie live in Mexico
• Living in almost what feels like two worlds here. The ex-pat community is very tuned into what's happening in the US and sheltering in place

• Our situation hasn't changed financially. I think that at the time we had hopes that we could raise some money or at least get alone. We're not even pursuing that at this point
• We're certainly used to bootstrapping and feeling that stress and coming up with interesting solutions to our cash problems.

• We have had a couple of requests for enterprise plans, one existing customer that has a lot of data that they need to be migrated over and they have a custom feature that they want
• Then a new customer who has a custom feature in data migration.
• It's unexpected. Feasibly you think they're going to cut back expenses, but larger deals are coming your way.
• The churn that we have had has been largely solo designers and smaller firms
• One of the things of going upmarket, the typical pattern is there price sensitive, they churn less.
• We've had a lot of inbound interest and a lot of them are saying things like now that we're home working remotely, we're sort of investigating better ways to work online

• Across the portfolio of companies that are part of TinySeed, there is about 15% that are having real struggles with the impact of the pandemic on the industry they serve. Another 70% are waiting to see what happens, perhaps cutting back on expenses and generally seeing a growth plateau. Then, there's the 15% of companies for whom remote work is a boon and their growth is accelerating faster than ever.
• Gather has had to cut their developer contract in half
• Big features are kind of on hold for a little while
• Staying focused has just been difficult

• I think my biggest fear is that the trend that we've seen this month as being a big uptick in sales and opportunities is just a flash in the pan.
• In different times, we might be able to pivot if we needed to, but because of our financial situation it's going to be hard for us to pivot out of it
• Looking forward to seeing how these enterprise deals play out
• Trying to figure out ways that we could get customers to pay for some of the features that we'd like to build

Links from the show

• Gather | Website
• Brian Elliott | Twitter

This episode is a walk down memory lane as Rob shares the story of acquiring his first product 15 years ago. We hear how Rob navigated the purchase of the product, a potential partnership with a trusted friend, and pushing through when his back was against the wall.

Hopefully, this episode will inspire you to take action and keep shipping.

The topics we cover

[5:03] Three levels to making money online

[6:36] Discovering the original version of DotNetInvoice

[11:34] The business proposition

[15:10] The counteroffer from Rob's trusted friend

[18:41] Business plan vs boots on the ground

[20:49] Buying DotNetInvoice

If you enjoyed this episode, let us know by clicking the link and sharing what you learned.

Click here to share your number one takeaway from the episode.

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