Startups For the Rest of Us

Latest Episodes:

Episode 603 | Bootstrapping HotJar to $40M ARR Using D2C Marketing May 17, 2022

Show notes

In episode 603, Rob Walling chats with David Darmanin, one of the founders of Hotjar. Hotjar was bootstrapped to $40 million ARR with a fully distributed team of 170 employees. David and his cofounders sold the company for a 9-figure exit in 2021.

From their incredible launch story and their unique DTC approach to sales and marketing in a B2B SaaS business to David’s mental models and the thought process behind selling the business, there is no shortage of key insights in this episode.

Topics we cover:

[5:07] How David initially financed building Hotjar

[8:11] The biggest difference between Hotjar and its competitors

[12:03] The unique approach that David took when launching Hotjar

[12:44] Lessons learned from a failed product launch prior to Hotjar

[15:01] How they built their initial launch list to 60,000 subscribers

[19:32] How to know how much to spend on paid ads

[24:53] Why David said it was easy to work 60-80 hour workweeks for the first 6-9 months of Hotjar

[27:22] The two key ingredients needed if you want to sell a low-priced SaaS product

[30:31] How they tripled their growth from $1M - $3M in the first year

[33:26] How their initial launch strategy gave them a major competitive advantage when they started doing content marketing later on

[34:03] What led him to sell Hotjar

[40:39] How long the exit process took

Links from the Show:

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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Episode 602 | Explaining SaaS Metrics to a Child May 10, 2022

Show notes

In episode 602, Rob Walling explains SaaS metrics to his kid. This is a great episode to listen to if you are unfamiliar or not well-versed in SaaS because we dig into from first principles, starting with dollars, revenue, and the purpose of businesses, all the way to SaaS metrics like MRR, ACV, and LTV. And, even if you are well-versed in SaaS metrics, you’ll likely learn a few things from this conversation.

Episode Sponsor:

Microsoft for Startups Founder Hub

Microsoft for Startups is on a mission to help all founders innovate and grow no matter their background, location, or progress. Microsoft for Startups Founders Hub is a platform that provides founders with free resources to help solve startup challenges, including access to Azure credits, development tools like Github, mentorship resources, Microsoft collaboration and productivity software like Teams and Outlook and more. The program is open to all and takes 5 minutes to sign up, with no funding required.

Learn more aka.ms/startupsfortherestofus

Topics we cover:

[1:55] MicroConf Local London tickets are on sale

[3:17] Starting with the basics: money, dollars, and businesses

[7:01] Revenue

[7:12] Expenses

[10:51] SaaS

[13:29] Recurring revenue

[13:58] Average revenue per account (ARPA)

[14:56] Monthly recurring revenue (MRR)

[15:08] Average revenue per customer

[17:08] Annual contract value (ACV)

[18:18] Churn

[19:30] Differences between Revenue Churn and Customer Churn

[21:18] Lifetime value

[22:10] Average customer lifetime value

[25:49] Customer Acquisition Cost (CAC)

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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Episode 601 | Bootstrapping B2B vs. B2C May 03, 2022

Show notes

In episode 601, Rob Walling chats with Nick Fogle of ChurnKey. Nick previously cofounded Wavve which was acquired in early 2021. In this conversation, they chat about how the idea for Churnkey came from his other business, decision to sell Wavve, and some of the key differences between bootstrapping a B2C vs a B2B SaaS.

Topics we cover:

[2:11] Tips for reducing churn

[3:26] Asking for feedback at the point of cancellation via feedback surveys

[8:09] When he knew it was the right time to double down on ChurnKey

[9:06] A piece of advice for bootstrappers looking for SaaS business ideas

[14:44] The process Nick and his cofounder used to sell Wavve for a life-changing exit.

[22:13] The potential pitfalls of off-market deals

[26:56] His initial reaction after selling Wavve

[29:04] The key differences between selling B2B and B2C

[30:36] Why Nick made the difference to hire a head of sales for ChurnKey

[32:14] The mindset shifts he had to unlock around shifting from low touch to high touch sales

[33:43] Why he decided to join the current batch of TinySeed

Links from the Show:

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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Episode 600 | When to Hire Your First Manager + What You Should Be Focused On (A Rob Solo Adventure) Apr 26, 2022

Show notes

In episode 600, join Rob Walling for a solo adventure as he dives into topics ranging from when to hire your first manager to a mental framework for deciding which things to work on vs. what to delegate to your team. He also shares his thought process behind when things take multiple iterations and how to know whether or not you are on the right track.

Episode Sponsor:

Microsoft for Startups Founder Hub

Learn more aka.ms/startupsfortherestofus

Topics we cover:

[1:04] A mental framework for deciding what things you should focus on as a SaaS founder vs. what to delegate

[7:28] The importance of resting and taking proper breaks as a SaaS founder

[14:28] When to hire your first manager

[14:50] The two main components of management: supervising and leading

[18:45] The importance of continuous iterations

[26:21] Why you need to manage your own psychology as a founder

[28:11] Hitting a big podcast milestone: 600 episodes

Links from the Show:

Strawberry Fields I Beatles
Yesterday I Beatles
Episode 200: Customer Acquisition Plans for Bootstrappers

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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Episode 599 | Finding the Bootstrapper Hockey Stick Apr 19, 2022

Show notes

In episode 599, Rob Walling chats with Dominic “Dom” and Tracy Phillips of CodeSubmit. CodeSubmit provides a library of real-world, take-home tasks in more than 60 coding languages. Some of their customers are Audi, Netflix, Carbon Health, 3M, and Apple.

Dom and Tracy were also a part of the spring 2020 batch of TinySeed. During that year, they managed to 25x their MRR. In this episode, we’re digging into how they did that, what led to their bootstrapped hockey stick growth moment, what it is like working on a company with your spouse, and much more.

Topics we cover:

[2:20] How Dom and Tracy came up with the idea for CodeSubmit

[6:59] The approach they used to build their product MVP on nights and weekends

[11:16] Running a startup with your spouse

[13:42] The catalyst that led to their hockey stick growth moment

[17:06] When they knew they had product market fit

[21:46] The number of different marketing channels they tried before they decided to double down on content marketing and SEO

[26:19] The biggest mistakes that hiring managers and recruiters make when vetting new developers via take-home challenges

[29:40] Thoughts on building a lifestyle business

Links from the Show:

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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Episode 598 | Diversity, Mission & Values, How to Start, and More Listener Questions Apr 12, 2022

Show notes

In episode 598, join Rob Walling as he answers listener emails. Topics range from diversity in the startup ecosystem and when’s the right time to write your company’s mission, philosophy, and values to how to find good business ideas and the different approaches for developing features for a new app.

Episode Sponsor:

Microsoft for Startups Founder Hub

Learn more aka.ms/startupsfortherestofus

Topics we cover:

[1:21] MicroConf Remote 4.0

[1:59] Improving diversity in the startup ecosystem

[8:11] Is bootstrapping the great equalizer in business?

[8:51] The right time to work on company values, mission statements, and philosophy

[14:02] Developing features for a new app

[15:18] How to figure out your minimum lovable product

[21:18] How to find business ideas

Links from the Show:

State of Independent SaaS
The Updated Survival Guide for Bootstrapping SaaS I MicroConf On Air
Episode 589 I Finding a SaaS idea through 70 cold calls
My First Million
Tropical MBA

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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Episode 597 | The Challenge of Building a Business in a Regulated Industry Apr 05, 2022

Show notes

In episode 597, Rob Walling chats with Ashley Baxter, the founder of With Jack. With Jack gives peace of mind and protection for UK freelancers through insurance, professional indemnity, public liability, contracts, legal expenses, etc.

We dig into the lessons Ashley learned from a failed insurance business she inherited from her father, how she used her freelance photography to fund With Jack in the early days, along with sharing many of the successes and failures she has had on her entrepreneurial journey.

Topics we cover:

[1:49] Tickets for MicroConf Remote 4.0 are now on sale

[2:55] Putting a tech twist on a regulated industry

[3:27] Improving the onboarding experience

[5:24] How Ashley came up with the name for her business, With Jack

[8:24] How she used the money from her freelance photography business to fund the early development costs for With Jack

[10:16] Lessons learned from taking over her father’s insurance business at 18

[15:20] The danger of depending on only one channel to run your business

[17:49] Ashley’s three pivotal business moments

[21:27] The concept of a vitamin vs. painkiller business

[27:10] The challenges of hiring an executive or admin assistant in a highly regulated industry

[28:42] How Ashley responded when a competitor stole her website design

[31:17] Why you shouldn’t be intimidated if a competitor gets funding

Links from the Show:

Ashley Baxter @iamashley I Twitter
With Jack I Company Website
Ashley Baxter I Ashley’s website

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

Episode 596 | News Round-Up: Google Ends WFH, Founder Salaries, How to Use Email Mar 29, 2022

Show notes

In episode 596, Rob Walling is joined by Einar Vollset and Tracy Osborn for a bootstrapper news roundup episode. They cover a wide range of topics from Google’s decision to bring employees back into the office (and the potential implications for bootstrapped companies), founder salary data trends, email management strategies, and much more.

Episode Sponsor:

Microsoft for Startups Founder Hub

Learn more aka.ms/startupsfortherestofus

Topics we cover:

[0:59] The State of Independent SaaS Report & Livestream

[5:38] Google is ending work from home options for most Bay Area employees

[12:11] How much do startup founders pay themselves?

[14:51] The impact on having cofounders and salaries

[19:41] Why you are probably using email wrong

[26:21] Rob’s system for filtering emails

[30:45] Twitter is making it harder to choose the reverse chronological feed

[37:37] Practical strategies for working with and getting money to your existing developers in Ukraine and Russia

Links from the Show:

Google mandates workers back to Silicon Valley, other offices from April 4 I Reuters
What do startup founders pay themselves? I Sifted
Twitter makes it harder to choose the old reverse-chronological feed I The Verge

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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Episode 595 | TinySeed Tales Season 2: Where Are They Now? Mar 22, 2022

Show notes

In episode 595, Rob Walling catches up with Brian and Scottie Elliott, the husband and wife co-founders of Gather, an interior design project management SaaS. This husband and wife duo shared their victories, challenges, and failures, including a cash crunch, moving upmarket, and managing to double revenue over their nine episodes of TinySeed Tales Season 2.

It’s been over a year since they were last on the podcast and wanted to see how the company is doing. It turns out Gather is on track to 10x their MRR.

In this episode, we reflect on what they learned in the last year, how their thought process has evolved around deploying capital to grow the business, and what they are most excited about in 2022.

Topics we cover:

[3:33] How Gather is on track to 10x MRR

[4:26] Shifting from solo designers and small design firms to catering to large firms

[5:51] Moving upmarket

[8:28] Why they shut down Gather consulting services

[10:38] How they knew when they had product-market fit

[12:57] How they bounced back after their developer accidentally crashed their entire app

[20:11] Their thought process for deploying capital to grow the business

[23:02] What they are most excited about in 2022

Links from the Show:

Gather | Website
Brian Elliott (@brianleeelliott) | Twitter

Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out all of Season 2 of TinySeed Tales with Brian and Scottie and Season 1 of TinySeed Tales, where we follow the SaaS journey with Craig Hewitt of Castos.

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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Episode 594 | Starting Over with the TropicalMBA's Dan & Ian Mar 15, 2022

Show notes

In Episode 594, Rob Walling chats with Dan Andrews and Ian Schoen, the founders of Dynamite Jobs and the TropicalMBA podcast. We talk about how they started over. They started a new business, Dynamite Jobs, a couple of years after selling their physical products company back in 2015.

Episode Sponsor:

Microsoft for Startups Founder Hub

Learn more aka.ms/startupsfortherestofus

Dynamite Jobs was born after seeing a need within their community, The Dynamite Circle, a community for location independent entrepreneurs. It’s a need that would be hard for most people to bootstrap because it is a two-sided marketplace, but Dan and Ian had an advantage with their existing business and audience, and were able to capitalize on it.

In fact, after humble beginnings, the business has grown 10x in the last year.

In this episode, we chat about how they are bootstrapping and growing a two-sided marketplace, along with a wide range of other topics.

Topics we cover:

[2:37] Why Dan and Ian both settled in Austin, Texas and the unexpected benefits that has had for their businesses

[3:22] Why their digital nomad journey in the early days was born out of necessity

[4:35] The events that led to the first DCBKK event in 2012 and the impact it had on their business

[6:16] Embracing the chops index instead of the old school digital marketer “guru” model

[8:21] The ideas that led Dan and Ian to start Dynamite Jobs in 2017

[14:46] The first key metric for Dynamite Jobs back in the early days

[17:12] How deciding to hire a CTO was the catalyst that scaled Dynamite Jobs exponentially in late summer 2020

[20:34] The critical mistake they made that cost them months of development time

[22:51] The concept of CEO bombing vs. diving deeper into the core features that matter

[24:53] The 1000 day principle

[28:14] Where Dynamite Jobs is in relation to the 1000 day principle

[29:00] How they 10x’ed the revenue for Dynamite Jobs in 2021

[30:26] The value of hiring senior people who are better than you

[35:59] Actionable tips for recruiting and hiring great people

[38:44] The lowest cost, highest leverage hiring advantage for founders

[41:21] The rip, pivot and jam framework

[43:14] Why some of their “best ideas” turned out to be the biggest failures

Links from the Show:

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