Harris Kenny was a long-time listener of the podcast, and dreamed about building his own software product. After multiple attempts, over 5 years, he finally did it. How? He shares his experiences transitioning from a corporate job to entrepreneurship. He also discusses the challenges of user engagement, the exploration of various SaaS ideas, and the importance of foundational work in entrepreneurship.

Links:

• Harris Kenny on Linkedin
• OutboundSync - Integrate outbound campaigns in HubSpot and Salesforce
• IntroCRM (Archived) - Access Blocked
• How Loom Found PULL - Growth Strategy Case Study
• Follow Justin on Bluesky

Have feedback on this episode?

• 👉 ​Leave a voicemail here​
• 🦋 Reply on Bluesky

Timestamps:

• (00:09) - I did it! I build my saas!
• (02:59) - Why did Harris quit his job?
• (11:03) - When you don't have a boss, do you have the drive to go get work?
• (15:45) - How did you hear about saas businesses?
• (27:02) - Recognizing a need and building something for it
• (34:44) - So many opportunities in inventory software
• (41:03) - The difficulty of getting people to just log in
• (49:18) - The saas that worked
• (01:01:01) - Where are you getting new customers from?
• (01:06:47) - Using Tinyseed as a bridge
• (01:11:02) - Going over the top on support is a key
• (01:24:04) - Showing results helps agencies show value

• Pascal from sharpen.page
• Rewardful.com
• Greg Park
• Mitchell Davis from RecruitKit.com.au
• Marcel Fahle, wearebold.af
• Bill Condo (@mavrck)
• Ward from MemberSpace.com
• Evandro Sasse
• Austin Loveless
• Michael Sitver
• Colin Gray
• Dave Giunta

🎙️ Podcast hosting is provided by Transistor.fm.
📺 Learn how to start your own podcast!

Bootstrapping a business is like getting a plane to lift off the ground. But what do you do once the plane is in the air?

Dave Giunta and Justin Jackson recorded a recent phone call about maintaining motivation after the initial startup phase. How does founder energy shift once you've achieved your early goals? Dave prods Justin to find new sources of motivation – whether through mentoring junior team members, connecting with customers in fresh ways, or knowing when it's time to explore new horizons.

They also discuss why Dave left Home Chef (after 8 years) and what he's doing next.

Links:

• Follow Dave on Bluesky
• Connect with Dave on LinkedIn
• Follow Justin on Bluesky

Have feedback on this episode?

• 👉 ​Leave a voicemail here​
• 🦋 Reply on Bluesky

Timestamps:

• 00:00:17 - Giuuuuuunta
• 00:01:15 - Chatting in Guatemala: maintaining motivation, remote work, career transitions
• 00:02:12 - Motivation in early vs late stage startups
• 00:06:00 - Challenges with maintaining motivation once the business is established
• 00:15:35 - Working with different team member motivations
• 00:26:42 - Importance of understanding individual team members
• 00:29:20 - Remote work advantages and challenges
• 00:35:35 - Working with junior team members and mentorship
• 00:54:00 - Why Dave left Home Chef after 8+ years
• 00:57:00 - Discussion of career transitions and giving yourself space to explore
• 01:02:20 - Future plans and exploration after leaving long-term role

Thanks to our monthly supporters

• Pascal from sharpen.page
• Rewardful.com
• Greg Park
• Mitchell Davis from RecruitKit.com.au
• Marcel Fahle, wearebold.af
• Bill Condo (@mavrck)
• Ward from MemberSpace.com
• Evandro Sasse
• Austin Loveless
• Michael Sitver
• Colin Gray
• Dave Giunta

🎙️ Podcast hosting is provided by Transistor.fm.
📺 Learn how to start your own podcast!

How do founders of small bootstrapped companies hire new employees?

Adam Wathan got over 1600 people who applied for two new roles at Tailwind Labs (a small team of six people). They ended up hiring two people, but neither of them actually applied. This wasn't how Adam expected (or hoped) this process would go. There were lots of surprising takeaways and lessons learned from the whole experience.

Links:

• Hackers Inc podcast
• Tailwind job opening announcement
• Design Engineer job posting
• Staff Software Engineer job posting
• Reddit: 11 months of job searching visualized

Have feedback on this episode?

• 👉 ​Leave a voicemail here​
• 🐦 Reply on Twitter

Timestamps:

• (03:40) - What's the size of Transistor and when did you last hire?
• (05:24) - How did you meet or find your employees?
• (07:12) - Adam's process for hiring
• (12:44) - The energy required to process applications
• (17:32) - What got people in to the 100 list?
• (21:03) - Did Adam get any videos in applications?
• (24:49) - Previous employment was a good indicator
• (30:16) - Painting a picture of what the position looks like
• (32:02) - The kinds of people who applied
• (34:52) - How did the application process work out?
• (38:52) - The kinds of questions we asked applicants
• (42:25) - Does a great conversation impact a hiring decision or not?
• (49:24) - Does having the position open in public help?
• (51:36) - How Adam was connected to the people they hired
• (59:31) - The importance of conference conversations
• (01:02:20) - Finding ways to share your work in public
• (01:06:11) - The process does work... just not this time
• (01:12:30) - Could I ever get comfortable with a 70% success rate?
• (01:20:53) - Bringing in someone you knew vs a fan
• (01:26:45) - Keeping a tab in different areas to pull from

Thanks to our monthly supporters

• Pascal from sharpen.page
• Rewardful.com
• Greg Park
• Mitchell Davis from RecruitKit.com.au
• Marcel Fahle, wearebold.af
• Bill Condo (@mavrck)
• Ward from MemberSpace.com
• Evandro Sasse
• Austin Loveless
• Michael Sitver
• Colin Gray
• Dave Giunta

🎙️ Podcast hosting is provided by Transistor.fm.
📺 Learn how to start your own podcast!