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Overcoming SMB Roadblocks: Expert tips from Gusto's Josh Reeves | Episode 1988

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Manage episode 432142628 series 3371599
Content provided by Jason Calacanis. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Jason Calacanis or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

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:

X: https://x.com/joshuareeves

LinkedIn: https://www.linkedin.com/in/joshuareeves

*

Follow Alex:

X: https://x.com/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

  continue reading

1094 episodes

Artwork
iconShare
 
Manage episode 432142628 series 3371599
Content provided by Jason Calacanis. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Jason Calacanis or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

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:

X: https://x.com/joshuareeves

LinkedIn: https://www.linkedin.com/in/joshuareeves

*

Follow Alex:

X: https://x.com/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

  continue reading

1094 episodes

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