Logo

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

    en-usAugust 02, 2024
    Why is organic growth important for startups?
    What was the inspiration behind Gusto's creation?
    How does Gusto prioritize data security?
    What are Gusto's three main go-to-market strategies?
    What role do partnerships play in Gusto's success?

    Podcast Summary

    • Product Love and Organic GrowthCreating a product that people love is crucial for startups, especially those serving smaller businesses, as organic growth through word of mouth and referrals can lead to more top of funnel leads. Prioritizing data security and privacy is also essential when handling sensitive customer information.

      Building a product that people love and creating organic growth through word of mouth and referrals is crucial for startups, especially those serving smaller businesses where revenue per customer is less. This is because paid acquisition alone may not be sufficient. A product that is super useful and valuable to customers will encourage them to share and evangelize, leading to more top of funnel leads. Gusto, a unicorn HR tech company worth nearly $10 billion, is a prime example of this strategy in action. The co-founder and CEO, Josh Reeves, shared his journey from his early days at Zazzle to starting Unwrap and selling it in 2010. The experience of running payroll for his small team during that time sparked the idea for Gusto, which aimed to make payroll and HR processes more digital-friendly for small businesses. Additionally, the importance of security and compliance, highlighted by the recent CrowdStrike incident, cannot be overlooked by startups handling sensitive customer data. From the beginning, Gusto prioritized data security and privacy, understanding the responsibility that comes with handling crucial information for their clients.

    • Security in Payroll and HRPayroll and HR tech company Gusto prioritizes security and reliability, handling financial data and corporate accounts, maintaining a secure system crucial as they process over half a trillion dollars annually and face increasing cybersecurity concerns.

      Gusto, a payroll and HR technology company, has prioritized reliability and security since its early days, even when it was a small team. With the handling of financial data and access to corporate accounts, Gusto understands the importance of maintaining a secure system and processing payroll accurately. As the company has grown to 2,600 employees and processes over half a trillion dollars annually, this focus on security remains crucial. The economic climate and increasing cybersecurity concerns add to the importance of maintaining a secure system. The balance lies in working with a system that is obsessed with security while also creating awareness, solving problems for customers, and providing more value over time.

    • SMB go-to-market strategies for GustoGusto targets SMB market by offering great technology, forming partnerships with accounting firms, embedding payroll solutions in other companies, and directly selling to SMBs. Building a loved product is crucial for success due to the importance of organic leads.

      Successful companies in the small and medium-sized business (SMB) segment focus on bringing great technology to this market, which is full of opportunities due to the shift from manual processes to cloud-based systems. Three main go-to-market strategies for Gusto include: 1) partnerships with accounting firms, 2) embedded payroll solutions for other companies, and 3) direct sales to SMBs. The accounting firm partnership model, which began in 2013, allows these firms to add their clients to Gusto, saving them time and offering higher-value services. The embedded payroll model, launched in 2021, enables other companies to use Gusto's technology inside their services, providing a native payroll experience for their small business customers. Lastly, the direct sales strategy focuses on acquiring new SMB customers through a multi-product setup that ensures strong long-term net dollar retention and can offset higher gross churn. A key ingredient for success in the SMB segment is building a product that people love, as organic word-of-mouth and referrals are crucial for generating top-of-funnel leads.

    • Customer support systemA simple and effective customer support system can significantly improve the customer experience and make a product more appealing. Prioritize focusing on a niche market, delivering essential services, and expanding based on customer feedback to create a positive customer experience.

      Having a simple and effective customer support system, like OpenPhone's shared number solution, can significantly improve the customer experience and make your product more appealing. Gusto, a company that offers payroll and HR solutions for small businesses, emphasizes the importance of focusing on a niche market and delivering essential services that are widely needed. To expand and serve existing and future customers, Gusto prioritizes adding products based on customer feedback and proving a "better together" dimension. They also strive to keep their products simple and easy to use as they grow more powerful. By focusing on these principles, companies can effectively serve small businesses and create a positive customer experience.

    • Creating lovable products for SMBsSimplify and make products intuitive for SMBs, create a 'wow' factor, prioritize empathy and customer proximity for successful product development

      For businesses targeting small and medium-sized enterprises (SMBs), creating easy-to-use, lovable products is crucial for success. SMB owners are often overwhelmed with various responsibilities and don't have the luxury of large departments or staff. Therefore, simplicity and intuitiveness are essential. Additionally, creating a product that elicits a "wow" factor, making the users' lives easier and simpler, can lead to virality and positive word-of-mouth. Empathy and customer proximity should be prioritized throughout the organization to ensure that the product development team truly understands the needs and pain points of their customers. This approach not only benefits SMBs but also larger enterprises, as delivering lovable products can lead to increased accountability and long-term success.

    • Organic growth and content strategyFocusing on organic growth and creating valuable content for small businesses can help build strong relationships and establish a brand, while paid acquisition can be added later as a complementary strategy.

      For Gusto, a successful business model relies heavily on organic growth and building strong relationships with small businesses through content and excellent customer service. When they launched in 2012, they focused solely on organic growth for the first year without any paid acquisition. They believed that gambling on growth through paid marketing was not sustainable for their business model, which is based on monthly billing and providing various products to companies. Instead, they focused on creating useful content for small businesses, which helped build awareness for their brand. After a year, they started layering in paid acquisition. Now, they see their go-to-market strategy as a portfolio of activities, including content, organic growth, and paid acquisition, all working together to drive awareness and conversions. They aim to be more than just a transactional tool for small businesses but a partner, providing proactive solutions and automating tasks to make entrepreneurship easier.

    • Payroll and HR market size and importanceThe payroll and HR market is large and crucial due to the fundamental need for people to earn and spend money, leaving room for growth for companies like Gusto that focus on providing digital solutions for small and medium-sized businesses

      The market for companies focused on payroll and HR solutions is larger than many may realize, as it addresses foundational needs in a capitalist economy. Gusto, a player in this space, has seen significant growth alongside competitors due to the digital transformation and the vast potential for converting pen-and-paper businesses to digital solutions. The market's size and importance stem from the need for people to earn and spend money, making payroll a crucial pain point for businesses. Additionally, the fragmented nature of the market leaves room for new entrants to capture a significant share. Gusto, with its focus on serving small and medium-sized businesses, aims to provide real solutions for its customers and grow as a valuable company by executing its vision. The company's approach contrasts with some peers who may prioritize loud external conversations, and Gusto instead chooses to focus on building great products and serving its customers.

    • Customer-centric approachA customer-centric approach in business communications can help avoid conflicts and focus on providing solutions for customers, as demonstrated by Gusto's efforts to simplify complex technology, address compliance and regulatory issues, and enable international hiring for small businesses

      Having a customer-centric approach in business communications can help avoid conflicts and focus on providing solutions for customers. Gusto, a company that aims to bring enterprise-level technology to small businesses, emphasizes this philosophy. They believe that companies exist to serve and solve customer pain points, and they hire team members who share this belief. The company's efforts include simplifying complex technology, addressing compliance and regulatory issues, and enabling international hiring. By focusing on the needs of small businesses and providing tools that were once only available to larger companies, Gusto aims to level the playing field and help small businesses grow and thrive.

    • Gusto's expansion strategiesGusto expands its reach to small businesses through brand advertising, potential sports sponsorships, and new product development. Achieving free cash flow positivity, Gusto plans to reinvest in engineering, go-to-market engines, and future public offering.

      Gusto, a payroll and HR platform, is expanding its reach to more small businesses through various products and go-to-market strategies, including brand advertising and potential sponsorships of sports teams. This multi-faceted approach allows the company to build stronger relationships with its audience and scale effectively. Gusto has recently achieved free cash flow positivity and plans to reinvest that money into new product development, engineering hiring, and go-to-market engines. Despite the trend of waiting until reaching a billion dollars in Annual Recurring Revenue (ARR) to go public, Gusto aims to prioritize helping people and plans to become a public company in the future. The company values a service mindset, humility, and ambition in its team members. Overall, Gusto's focus on growth, innovation, and serving its customers sets it apart in the private market technology landscape.

    Recent Episodes from This Week in Startups

    Relationship Advice of the Investor Sort with Meghan Reynolds of Altimeter | E2008

    Relationship Advice of the Investor Sort with Meghan Reynolds of Altimeter | E2008

    This Week in Startups is brought to you by…

    LinkedIn Ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to https://www.linkedin.com/thisweekinstartups

    Runway. Looking to up-level your financial planning Runway is the modern and intuitive way to model, plan, and align your business for everyone on your team. Sign up at ⁠https://www.Runway.com/TWIST to get your first 3 months free.

    Beehiiv. Power your newsletters with AI tools, referral programs, and ad network features—all in one platform. Get 30 days free and 20% off your first 3 months at ⁠https://www.Beehiiv.com/TWIST

    *

    Todays show:

    Meghan Reynolds takes the stage at Liquidity Summit 2024 to discuss the intricacies of raising capital and pitching to VCs. Meghan dives into many topics including the importance of relationships (3:07), fund size rationalization (20:36), market sentiment (25:55), and other crucial aspects of successful fundraising!

    *

    Timestamps:

    (0:00) Meghan Reynolds takes the stage at Liquidity Summit 2024

    (3:07) Meghan Reynolds’ talk “Relationship Advice: Of the LP / GP Sort”

    (9:43) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups

    (10:59) Client service in investor relations and fundraising strategies

    (15:07) The complexity factor in raising capital

    (19:19) Runway - Sign up at https://runway.com/twist to get your first 3 months free.

    (20:36) Rationalizing fund size, securing re-ups, and worst pitching practices

    (25:55) Market sentiment and single deal SPV dynamics

    (29:34) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist

    (31:02) VC allocations, private credit, and market dynamics

    *

    Subscribe to the TWiST newsletter: https://www.ticker.thisweekinstartups.com

    *

    Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

    *

    Check out Altimeter: https://www.altimeter.com

    *

    Follow Meghan X: https://x.com/MeghanKReynolds

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

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners:

    (9:43) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups

    (19:19) Runway - Sign up at https://runway.com/twist to get your first 3 months free.

    (29:34) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist

    *

    Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

    *

    Check out Jason’s suite of newsletters: https://substack.com/@calacanis

    *

    Follow TWiST:

    Substack: https://twistartups.substack.com

    Twitter: https://twitter.com/TWiStartups

    YouTube: https://www.youtube.com/thisweekin

    Instagram: https://www.instagram.com/thisweekinstartups

    TikTok: https://www.tiktok.com/@thisweekinstartups

    *

    Subscribe to the Founder University Podcast: https://www.founder.university/podcast

    This Week in Startups
    en-usSeptember 13, 2024

    The New Power Law & How I Built a $100B Portfolio | E2007

    The New Power Law & How I Built a $100B Portfolio | E2007

    This Week in Startups is brought to you by…

    .Tech Domains. Don’t miss our “Jam with JCal” contest! To apply and get more details go to jamwithjcal.tech brought to you by .tech domains.

    Fidelity Private Shares. Manage your cap table and data room, get faster, more accurate 409A valuation and fully automate your next financing round. Visit https://www.fidelityprivateshares.com/ Mention our podcast and receive 20% off your first-year paid subscription.

    Oracle. Oracle Cloud Infrastructure, or OCI, is a single platform for your infrastructure, database, application development, and AI needs. Save up to 50% on your cloud bill at https://www.oracle.com/twist

    *

    Timestamps:

    (0:00) Jason joins Pejman Nozad and Jason Shuman at the Liquidity Summit 2024.

    (3:25) Pejman Nozad’s “How I Built a $100B Portfolio”

    (10:42) .Tech Domains. Don’t miss our “Jam with JCal” contest! To apply and get more details go to https://jamwithjcal.tech/

    (21:34) Fidelity Private Shares. Visit https://www.fidelityprivateshares.com/ Mention our podcast and receive 20% off your first-year paid subscription.

    (23:50) Jason joins Pejman for a fireside chat.

    (36:33) Oracle. Save up to 50% on your cloud bill at https://www.oracle.com/twist

    (38:02) Jason Shuman’s “The New Power Law: Good vs Great Funds”:


    Subscribe to the TWiST newsletter: https://www.ticker.thisweekinstartups.com

    *

    Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

    *

    Check out Pear: https://pear.vc/

    Check out Primary: https://www.primary.vc/

    *

    Follow Pejman Nozad: X: https://x.com/pejmannozad

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

    *

    Follow Jason Shuman:

    X: https://x.com/JasonrShuman

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

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners:

    (10:42) .Tech Domains. Don’t miss our “Jam with JCal” contest! To apply and get more details go to https://jamwithjcal.tech/

    (21:34) Fidelity Private Shares. Visit ****https://www.fidelityprivateshares.com/ Mention our podcast and receive 20% off your first-year paid subscription.

    (36:33) Oracle. Save up to 50% on your cloud bill at https://www.oracle.com/twist

    *

    Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

    *

    Check out Jason’s suite of newsletters: https://substack.com/@calacanis

    *

    Follow TWiST:

    Substack: https://twistartups.substack.com

    Twitter: https://twitter.com/TWiStartups

    YouTube: https://www.youtube.com/thisweekin

    Instagram: https://www.instagram.com/thisweekinstartups

    TikTok: https://www.tiktok.com/@thisweekinstartups

    *

    Subscribe to the Founder University Podcast: https://www.founder.university/podcast

    This Week in Startups
    en-usSeptember 11, 2024

    Boom: Supersonic speeds for everyday travel with Blake Scholl | E2006

    Boom: Supersonic speeds for everyday travel with Blake Scholl | E2006

    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

    Squarespace. Turn your idea into a new website! Go to https://www.Squarespace.com/TWIST for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

    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

    *

    Todays show:

    Boom Supersonic’s Blake Scholl joins Jason to discuss the future of supersonic flight (1:18), Boom's vision and test flights (9:25), the evolution of hardware startups (22:29), the future of autonomous aviation (1:17:06), and much more!

    *

    Timestamps:

    (0:00) Boom Supersonic’s Blake Scholl joins Jason

    (1:18) Commercial flight speed & Concorde history

    (8:34) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

    (9:25) Boom's XB-1 test flights and airline partnerships

    (15:04) Pricing, market comparison, and venture capital's view on hardware startups

    (21:16) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

    (22:29) Evolution of startup market and hardware innovation

    (29:03) Boeing's innovation decline and attracting talent to projects

    (36:15) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist

    (37:42) Working with tech legends and overcoming engine design challenges

    (49:14) Cross-discipline innovation

    (57:01) Learning from Air France 447 and cockpit safety design

    (1:03:36) Cockpit technologies and the MH370 mystery

    (1:11:30) Public perception of aviation risks and airport security impact

    (1:17:06) The future of autonomous aviation

    *

    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 Blake:

    X: https://x.com/bscholl

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

    Check out: https://boomsupersonic.com / https://x.com/boomaero

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners:

    (8:34) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

    (21:16) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

    (36:15) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist

    *

    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

    This Week in Startups
    en-usSeptember 11, 2024

    Scaling Childcare with Tech: Winnie.com’s Blueprint for Growing with Purpose & Profit | E2005

    Scaling Childcare with Tech: Winnie.com’s Blueprint for Growing with Purpose & Profit | E2005

    This Week in Startups is brought to you by…

    Brave Search API. Get started for free at ⁠https://www.brave.com/jason

    CLA. Get started now at ⁠https://www.claconnect.com

    Sprig**.** Visit https://sprig.com/twist to book a demo and get a $75 gift card.

    *

    Timestamps:

    (0:00) Sara Mauskopf, CEO of Winnie joins Alex

    (1:45) Winnie's evolution, pivot, and focus on childcare services (7:25) Building Winnie's database and reflections on company growth

    (9:55) Brave Search API. Get started for free at ⁠https://www.brave.com/jason

    (12:08) The value of transparency and growth metrics

    (19:20) CLA. Get started now at ⁠https://www.claconnect.com/

    (21:16) Market positioning, motivations, and goals in the childcare industry (23:30) Addressing gender dynamics and startup funding (27:34) Balancing investor expectations with business models

    (29:43) Sprig. Visit https://sprig.com/twist ****to book a demo and get a $75 gift card.

    (31:10) Profitability, operational efficiency, and managing costs (37:01) Marketing strategies, brand growth, and the impact of Google’s model (40:30) Adapting to changing childcare demands due to remote work (44:08) Efforts to reduce childcare costs and home-based business challenges (50:06) Balancing profitability with growth and venture capital experiences (54:00) SaaS pricing challenges and the impact of AI (58:22) Tech M&A, FTC regulations, and innovation policies

    *

    Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/

    Check out the TWIST500: twist500.com

    Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

    *

    Check out: Winnie: https://winnie.com/

    Check out 2024 Inc. 5000 list: https://www.inc.com/inc5000/2024

    Check out the BLS statistics: https://www.bls.gov/cps/telework.htm#data

    *

    Follow Sara:

    X: https://x.com/sm

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

    *

    Follow Alex:

    X: https://x.com/alex

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

    *

    Thank you to our partners:

    (9:55) Brave Search API. Get started for free at ⁠https://www.brave.com/jason

    (19:20) CLA. Get started now at ⁠https://www.claconnect.com/

    (29:43) Sprig. Visit https://sprig.com/twist to book a demo and get a $75 gift card.

    *

    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

    This Week in Startups
    en-usSeptember 09, 2024

    The Rise of Stablecoins with Circle’s Jeremy Allaire | E2004

    The Rise of Stablecoins with Circle’s Jeremy Allaire | E2004

    This Week in Startups is brought to you by…

    LinkedIn Jobs. A business is only as strong as its people, and every hire matters. Go to https://www.linkedin.com/twist to post your first job for free. Terms and conditions apply.

    Google Cloud. Accelerate your startup journey with the Google for Startups Cloud Program. Get up to $200K in Google Cloud credits – or up to $350K for AI startups – plus training and guidance. Apply at⁠ https://startups.google.com/twist

    Beehiiv. Power your newsletters with AI tools, referral programs, and ad network features—all in one platform. Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist

    *

    Todays show:

    Circle’s Jeremy Allaire joins Alex Wilhelm to discuss the growth of stablecoins (49:06), stablecoin market infrastructure (22:23), their impact on global financial systems (56:07), and more!

    *

    Timestamps:

    (0:00) Circle’s Jeremy Allaire joins Alex Wilhelm

    (2:08) Jeremy's early career and the evolution of the internet

    (5:28) Transition from Macromedia to Circle's founding

    (12:10) LinkedIn Jobs - Go to https://www.linkedin.com/twist to post your first job for free.

    (13:21) Bitcoin, stablecoins, and Circle's compliance

    (20:53) Google Cloud - Get up to $200K in Google Cloud credits – or up to $350K for AI startups – plus training and guidance. Apply at https://startups.google.com/twist

    (22:23) The current state and future of stablecoin market infrastructure

    (28:07) Integrating stablecoins with traditional finance

    (34:12) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist

    (35:40) Stablecoins' impact on global financial systems

    (41:30) Circle's business model, scalability, and blockchain potential

    (49:06) Growth of USDC and other currency stablecoins

    (51:10) USDC market cap trends and interest rates

    (56:07) Stablecoins in the global financial system and US regulation

    *

    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 Jeremy:

    X: https://x.com/jerallaire

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

    Check out: https://www.circle.com

    *

    Follow Alex:

    X: https://x.com/alex

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

    *

    Thank you to our partners:

    (12:10) LinkedIn Jobs - Go to https://www.linkedin.com/twist to post your first job for free.

    (20:53) Google Cloud - Get up to $200K in Google Cloud credits – or up to $350K for AI startups – plus training and guidance. Apply at https://startups.google.com/twist

    (34:12) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist

    *

    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

    This Week in Startups
    en-usSeptember 06, 2024

    Medium: Reaching Profitability while The Internet is Broken + CorePod | E2003

    Medium: Reaching Profitability while The Internet is Broken + CorePod | E2003

    This Week in Startups is brought to you by…

    Notion. Notion Projects combines project management with your docs, knowledge base, and AI. Try notion projects for free at notion.com/twist

    Brex. The financial stack founders can bank on. Brex knows cash is king for startups, so they built a banking experience that takes every dollar further. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/twist24

    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

    *

    Timestamps:

    (0:00) Tony Stubblebine of Medium joins Alex.

    (3:10) The broken internet and ad-based models

    (5:57) Impact of AI on content creation and platform quality

    (10:01) Medium's curation and financial model

    (11:18) Notion - Try notion projects for free at https://www.notion.so/twist

    (18:23) Medium's growth, geographic expansion, and AI translation

    (20:02) Brex - Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/twist24

    (22:05) AI-driven media platforms and the impact of AI spam

    (29:32) OpenPhone - TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist⁠

    (30:59) Medium's subscriber growth and financial milestones

    (34:35) AI data exclusivity and challenges in forming training data cohorts

    (41:26) Medium's venture scale potential, profitability, and mission

    (45:17) CEO's mindset and financial scaling towards 10 million subscribers

    (50:41) Tony's personal use of AI in his workflow

    (53:24) Future of AI in practical applications and business model disruption

    (57:09) Organizing content and the challenge of integrating different formats

    (1:02:19) Growth potential of niche markets and Medium's independence

    (1:06:23) Jam with JCal! Introduction to Ulan Abdurazakov and CorePod

    (1:07:27) Corepod product discussion and go-to-market strategy

    (1:17:23) Jason Calacanis's advice on testing and market validation

    *

    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

    *

    Check out Medium: https://medium.com/

    Check out CorePod: https://www.corepod.tech/

    Enter the Jam with JCal contest: https://www.jamwithjcal.tech

    *

    Follow Tony:

    X: https://x.com/tonystubblebine

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

    *

    Follow Ulan

    X: https://x.com/defoemark

    LinkedIn: https://www.linkedin.com/in/ulanbek-abdurazakov/

    *

    Follow Alex:

    X: https://x.com/alex

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

    *

    Thank you to our partners:

    (11:18) Notion - Try notion projects for free at notion.com/twist

    (20:02) Brex - Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/twist24

    (29:32) OpenPhone - TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist⁠

    *

    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

    This Week in Startups
    en-usSeptember 05, 2024

    Fundraising hurdles and M&A slowdown with Becki DeGraw | Wilson Sonsini Startup Legal Basics

    Fundraising hurdles and M&A slowdown with Becki DeGraw | Wilson Sonsini Startup Legal Basics

    Todays show: Wilson Sonsini Partner Becki DeGraw joins Jason on the latest edition of Startup Legal Basics! In this episode, they break down fundraising trends (1:33), the challenges of M&A (7:39), and the evolving regulations for tech companies (13:29).

    *

    Timestamps:

    (00:00) Wilson Sonsini partner Becki DeGraw joins Jason

    (1:33) Fundraising trends and investor expectations

    (3:57) Breakeven points and penny warrants

    (7:39) M&A slowdown and regulatory challenges

    (13:29) Proposals for M&A regulation reform

    (16:08) Compliance costs and cybersecurity for startups

    (19:58) Legal strategies for startups and data policies

    *

    Check Out Wilson Sonsini: ⁠⁠https://www.wsgr.com⁠

    *

    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 Becki:

    LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    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

    This Week in Startups
    en-usSeptember 05, 2024

    Superhuman 2.0: The AI edge, top productivity hacks, and the future of email | E2002

    Superhuman 2.0: The AI edge, top productivity hacks, and the future of email | E2002

    This Week in Startups is brought to you by…

    NetSuite. The number one cloud financial system that unifies accounting, financial management, inventory, and HR into a single platform. Giving you ONE source of truth. Download the CFO’s Guide to AI and Machine Learning today! Visit https://www.netsuite.com/twist

    Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://lemon.io/twist

    AssemblyAI. Get maximum value from voice data with AssemblyAI. Build powerful products and features for your end users on the industry’s leading speech-to-text models. Get 100 free hours to start building at https://www.assemblyai.com/twist

    *

    Todays show:

    Superhuman’s Rahul Vohra joins Jason to discuss the evolution of Superhuman. They delve into Superhuman's onboarding strategy (11:17), live demos of Superhuman's AI features (27:37), and explore AI's impact on team management (52:07), and more!

    *

    Timestamps:

    (0:00) Superhuman’s Rahul Vohra joins Jason

    (2:02) Rahul Vohra's background and Superhuman's pitch

    (6:33) Evolution and early challenges of Superhuman

    (9:59) NetSuite - Download the CFO’s Guide to AI and Machine Learning today! Visit https://netsuite.com/twist

    (11:17) Superhuman's onboarding strategy and customer feedback importance

    (20:55) New features in Superhuman 2.0 and multiplayer email

    (26:00) AI's impact on podcast production

    (26:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

    (27:37) Live demo of Superhuman 2.0

    (38:38) AssemblyAI - Get 100 free hours to start building at https://www.assemblyai.com/twist

    (40:08) Importance of documenting conversations and Superhuman for Sales

    (44:17) Live demo of Superhuman's “Ask AI” feature

    (52:07) AI's impact on productivity and team management

    (58:27) AI tools for productivity

    (1:07:26) AI's future as a chief of staff and email management

    *

    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 Rahul:

    X: https://x.com/rahulvohra

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

    Check out: https://superhuman.com

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners:

    (9:59) NetSuite - Download the CFO’s Guide to AI and Machine Learning today! Visit https://netsuite.com/twist

    (26:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

    (38:38) AssemblyAI - Get 100 free hours to start building at https://www.assemblyai.com/twist

    *

    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

    This Week in Startups
    en-usSeptember 04, 2024

    AI Demos: Gemini Gmail, Search GPT, Groq with Voice & Playground | E2001

    AI Demos: Gemini Gmail, Search GPT, Groq with Voice & Playground | E2001

    Timestamps:

    (0:00) Sunny joins Jason to jump into AI demos.

    (1:21) Analysis of Q4's impact on startups and Nvidia's market performance

    (5:09) Chip design advancements and AI prevalence in startup technology

    (8:12) Experiences with ChatGPT-4 and Google's Gemini in Gmail

    (10:14) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST

    (11:36) Discussion on generative AI: filtered vs. unfiltered content

    (19:50) Vanta. TWiST listeners can get $1,000 off for a limited time at ⁠https://www.vanta.com/twist

    (20:03) Importance of SOC 2 compliance and AI's role in LinkedIn

    (22:42) AI integration in Gmail and throwing AI at business problems

    (25:28) AI personalization tools and grading AI email integration

    (29:01) Micro1. Visit ⁠https://www.micro1.ai/twist⁠ to open a talent search and get a 2 week free trial per hire.

    (32:22) Deep dive into Search GPT functionalities and Google's AI search evolution

    (39:08) Practical AI search tests and Yelp's data integration

    (43:17) Ethical considerations in personalized AI technology

    (45:26) AI-powered product recommendations and monetization of AI models

    (51:44) Legal challenges in AI and generation of web apps

    (56:15) Exploring practical AI applications and Claude AI's app development

    (1:00:14) The era of building your own apps and fast image generation tools

    (1:02:12) Comparison of Playground and Canva, impact on graphic design

    (1:04:28) Groq's itinerary creation and the future of user interfaces

    (1:07:14) Closing remarks and acknowledgments



    Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

    *

    LINKS:

    Check out Gemini Gmail Chat: https://workspaceupdates.googleblog.com/2024/06/gemini-in-side-panel-of-gmail.html

    Check out Search GPT: https://chatgpt.com/search

    Check out Groq with Voice: https://groq.com

    Check out Claude: https://claude.ai/

    Checkout Playground: https://playground.com/design

    *

    Follow Sunny:

    X: https://twitter.com/sundeep

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

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners: (10:14) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST

    (19:50) Vanta. TWiST listeners can get $1,000 off for a limited time at ⁠https://www.vanta.com/twist

    (29:01) Micro1. Visit ⁠https://www.micro1.ai/twist⁠ to open a talent search and get a 2 week free trial per hire.

    *

    Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/

    Check out the TWIST500: twist500.com

    *

    Great 2023 interviews: Steve Huffman, Brian Chesky, 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.founder.university/podcast

    This Week in Startups
    en-usSeptember 04, 2024

    Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000

    Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000

    This Week in Startups is brought to you by…

    Squarespace. Turn your idea into a new website! Go to https://www.squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

    LinkedIn Ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to https://www.linkedin.com/thisweekinstartups

    Brex. the financial stack founders can bank on. Brex knows cash is king for startups, so they built a banking experience that takes every dollar further. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/twist24

    *

    Todays show:

    Jason and Alex kick off episode 2000! They reflect on TWiST’s origins and early episodes (1:48), highlighting notable guests and memorable moments (22:31). They also share fan messages, and insights from cohosts (46:05), and wrap up celebrating standout moments (1:04:14).

    *

    Timestamps:

    (0:00) Jason and Alex kick off the show

    (1:48) The origins and early days of TWiST

    (9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

    (11:03) Recollections of the first TWiST episodes

    (20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups

    (22:31) Highlighting notable guests and memorable early episodes

    (30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24

    (32:02) More on standout guests and the TWiST studio evolution

    (38:37) David Sacks makes his first appearance on TWiST

    (46:05) Messages from TWiST fans and cohosts

    (1:05:14) Celebrating standout moments and key highlights on the show

    (1:28:02) A special message from the Launch team

    *

    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

    *

    Mentioned on the show:

    https://www.youtube.com/watch?v=yZX4fUYo6C0&list=PL24nOpPUQlbZcij2Jo-KNUpWFDSrrQKtH

    https://www.youtube.com/watch?v=t3bmpMX2qQ4

    https://www.youtube.com/watch?v=SP7B0oWTR3o

    https://www.youtube.com/watch?v=2cdrCYrZIvI

    https://youtu.be/wM0pVE_b1KU?si=NM1pK-pz9tUQFOqr&t=1366

    https://www.youtube.com/watch?v=550X5OZVk7Y

    https://www.youtube.com/watch?v=6VOQnK7O2To

    https://www.youtube.com/watch?v=n1_z9oOdytA

    https://www.youtube.com/watch?v=aM1DDVq3_vs

    https://www.youtube.com/watch?v=TYA_vdHSD8w

    https://www.youtube.com/watch?v=qwhP7K3bFRI

    https://www.youtube.com/watch?v=3seTmyRbcHU

    https://www.youtube.com/watch?v=ANGHOQ2Cqtc

    https://www.youtube.com/watch?v=HL2wWE27CUI

    https://www.youtube.com/watch?v=BXEO3oJKINA

    https://www.youtube.com/watch?v=43MgbwQBDik

    https://www.youtube.com/watch?v=SfJtIibCx78

    *

    Follow Alex:

    X: https://x.com/alex

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

    *

    Follow Jason:

    X: https://twitter.com/Jason

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

    *

    Thank you to our partners:

    (9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

    (20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups

    (30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24

    *

    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

    This Week in Startups
    en-usAugust 30, 2024