This Week in Startups

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

02 Aug 2024

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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

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13:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

2ª PARTE | 06 ENE 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

3ª PARTE | 22 ENE 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

3ª PARTE | 04 MAR 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

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This Week in Startups

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

This episode hasn't been transcribed yet

Other recent transcribed episodes

13:00H | 21 DIC 2025 | Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

2ª PARTE | 06 ENE 2026 | EL PARTIDAZO DE COPE

3ª PARTE | 22 ENE 2026 | EL PARTIDAZO DE COPE

3ª PARTE | 04 MAR 2026 | EL PARTIDAZO DE COPE

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