Overcoming SMB Roadblocks: Expert tips from Gusto's Josh Reeves | Episode 1988
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 2 August 2024
⏱️ 65 minutes
🧾️ Download transcript
Summary
This Week in Startups is brought to you by…
Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist
OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist
DevSquad. DevSquad helps startups design better products. If you need UI and UX expertise and don’t want to hire an entire design team, head to http://devsquad.com/startups and book a call. Mention that you are coming from TWiST to get 10% off.
*
Todays show:
Josh Reeves joins Alex Wilhelm to discuss building a product people love (21:11), SMB challenges (23:56), growth strategies (36:47), and more!
*
Timestamps:
(0:00) Josh Reeves joins Alex Wilhelm
(2:16) Josh's previous startups and the early days of web development
(6:26) Transition to digital solutions and security for small businesses
(10:31) Gusto's growth, success metrics, and market penetration
(13:38) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
(14:30) Gusto's North Star, marketing strategies, and channel growth
(21:11) Building a product people love with good unit economics
(22:29) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(23:56) Challenges of selling to SMBs and Gusto's product expansion
(28:50) Maintaining simplicity in product development
(35:18) DevSquad - Visit https://www.devsquad.com/startups, book a call, and mention TWIST for 10% off!
(36:47) Ensuring product quality and the role of organic growth in marketing
(44:39) Competitive landscape in payroll and HR space
(48:54) Gusto's potential fintech ventures and communication styles among founders
(56:07) IT spending growth among SMBs and international expansion
(1:00:16) Navigating competition and partnerships
(1:01:41) Diversification of go-to-market strategies
(1:03:31) Financial strategies and thoughts on going public
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Follow Josh:
LinkedIn: https://www.linkedin.com/in/joshuareeves
*
Follow Alex:
LinkedIn: https://www.linkedin.com/in/alexwilhelm
*
Thank you to our partners:
(13:38) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
(22:29) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(35:18) DevSquad - Visit https://www.devsquad.com/startups, book a call, and mention TWIST for 10% off!
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Transcript
Click on a timestamp to play from that location
| 0:00.0 | You have to build a product that people love. That organic word of mouth and referral, |
| 0:04.8 | you know, is still the biggest driver of top-of-funnel and leads to gusto. |
| 0:08.9 | And that's because if you're serving smaller business, you're going to make less revenue per customer, so it can't just be a paid acquisition game. |
| 0:15.0 | You have to have something that's super useful, people want to evangelize, you know, share on social, etc. |
| 0:21.0 | And it has to be a key part of how you're creating you know more funnel and more |
| 0:24.4 | top of funnel leads into your product. |
| 0:27.1 | This weekend startups is brought to you by Vanta. |
| 0:31.5 | Compliance and security shouldn't be a dealbreaker for startups to win new business. |
| 0:36.0 | Vanta makes it easy for companies to get a Sawk 2 report fast. |
| 0:41.0 | Twist listeners can get $1,000 off for a limited time at vanta.com slash twist. |
| 0:48.0 | Open phone. Create business phone numbers for you and your team that work through an app on your smartphone or |
| 0:53.4 | desktop. Twist listeners can get an extra 20% off any plan for your first six months |
| 0:58.8 | at openphone.com slash twist twist and Dev Squad |
| 1:04.5 | Dev Squad helps startups design better products. If you need UI and UX expertise and don't want to hire an entire design team |
| 1:12.1 | head to Dev Squad.com slash startups and book a call. |
| 1:16.4 | mention that you're coming from Twist to get 10% off. |
| 1:20.0 | Hello and welcome back to this week in startups. |
| 1:22.4 | My name is Alex at Alex over on Twitter. |
| 1:25.6 | One of my favorite startup clusters in the entire world |
| 1:28.3 | is the HR tech space. |
| 1:30.5 | Now I know it's not quite as headline-grabbing as quantum computing or, I don't know, |
| 1:34.7 | drone-based deliveries, but it's incredibly important and so large that it's actually |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Jason Calacanis, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Jason Calacanis and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.