Ask Jason LIVE!: Unpacking Startup Strategies with Real-Time Q&A | E1921

Ask Jason LIVE!: Unpacking Startup Strategies with Real-Time Q&A | E1921

Jason kicks off another Ask Jason with 6 live guests! (00:00:00)

  • This episode of Weekend Startups is a live Q&A session with 6 live guests.
  • Viewers can submit questions to be mentored on various topics including startups, fundraising, life, technology, etc.
  • This Week in Startups is sponsored by Squarespace, OpenPhone, and Experimentation Platform Optimization (EPO).
  • Squarespace allows users to turn their ideas into new websites.
  • Viewers can get a free trial at
  • Use the offer code TWIST to save 10% off the first purchase of a website or domain.
  • OpenPhone creates business phone numbers for individuals and teams that work through an app on a smartphone or desktop.
  • Twist listeners can get an extra 20% off any plan for the first 6 months at
  • EPO is a tool that helps companies accelerate their experimentation velocity.
  • Viewers can visit to learn more about EPO.

Sean asks about investment firms changing how they invest early on. (00:01:13)

  • Convertible notes and SAFEs are early-stage investment structures that startups can use to raise capital without giving up too much equity.
  • Founders may decide not to raise subsequent funding rounds and instead run their businesses for profit, leading to negotiations with investors who hold convertible notes or SAFEs.
  • Founders and investors can extend the term of convertible notes or convert them into equity to resolve situations where founders do not want to buy out investors.
  • With the rise of AI, it is expected that more startups will be able to achieve sustainable growth without the need for external funding, leading to increased use of convertible notes and SAFEs.
  • Founder University, a program that teaches best practices for starting companies, is now offered quarterly.
  • Jason's startup accelerator program accepts 200 teams out of 2,000 applicants and invests in 10% of those teams, resulting in a 1% investment rate.
  • The program costs $500, but if participants complete all 12 weeks, they get the $500 back, which encourages a 94% completion rate.

Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain (00:11:42)

  • Squarespace has launched a new AI product called Blueprint AI, a guided design system for building new websites.
  • Blueprint AI generates a beautiful and custom website based on your preferred website structure, objective, color palette, design elements, and font pairings.
  • Squarespace is an all-in-one platform with powerful tools to launch and grow your business online.
  • With over a billion design combinations, you can create a unique online presence that reflects your brand and vision.
  • Try for a free trial and get 10% off your first website or domain purchase when you're ready to launch.

Pierson of jellypod asks about prioritizing multiple founders for investments or accelerators (00:13:28)

  • Successful venture-scale companies often have multiple co-founders, including a builder, designer, and growth hacker, as suggested by Paul Graham.
  • Solo founders face challenges in decision-making and have a higher failure rate compared to companies with multiple co-founders.
  • Investors prefer multiple co-founders for redundancy and reduced risk, increasing the chances of success.
  • Founder University emphasizes the importance of co-founders and only accepts 5% of solo founders.
  • Solo founders should critically assess their reasons for not having co-founders, as it may indicate issues with the idea, persuasion, or mindset.
  • Investing in startups with multiple co-founders and a launched product with paying customers can significantly reduce investment portfolio failures.
  • A founding team with significant equity (4% each) provides stability and motivation for long-term commitment.
  • Co-founders with large equity stakes (20-30%) have a strong incentive to stay with the company due to potential financial rewards.
  • Building a team with lower equity incentives may attract second-tier employees compared to co-founder level talent.
  • An idea to turn newsletters into podcasts using AI to read content and provide a daily digest of important news topics is considered a great idea with potential for success.
  • AI-powered tools like Speechify can convert text articles into audio format, offering an interesting concept for consuming business intelligence content.
  • The Jelly Pod app, available on the iOS app store, allows users to read emails in full within the app.

OpenPhone - Get 20% off your first six months (00:22:54)

  • OpenPhone simplifies business communications with an easy-to-use app.
  • It offers a shared phone number feature for teams to manage calls and texts efficiently.
  • OpenPhone is the top-rated business phone on G2 for customer satisfaction.
  • Twist listeners can get an extra 20% off any plan for the first 6 months at
  • OpenPhone can easily port existing numbers from other services at no extra cost.

Ask Jason LIVE!: Unpacking Startup Strategies with Real-Time Q&A (00:32:01)

  • Jason invites viewers to join the live Q&A session and ask questions about startups, fundraising, product-market fit, and more.
  • He prefers to answer questions without prior preparation for a more dynamic and genuine interaction.

Ann asks if they should raise venture capital to grow faster even though it means giving up some company ownership. (00:24:47)

  • Launching a minimum viable product (MVP) with limited resources can lead to a better product by focusing on solving customer problems.
  • Private beta testing provides valuable information about customer usage and preferences, reducing risks for potential investors who value a detailed understanding of customer behavior, engagement, and acquisition strategies.
  • A soft beta launch can test metrics and gather data on usage and referrals before a full launch.
  • Some companies, like Superhuman, have successfully maintained a perpetual beta status while still acquiring a large user base.
  • First-time entrepreneurs can increase their chances of securing venture capital by joining an accelerator or raising a seed round from a seed fund.
  • Founders University is a valuable resource for entrepreneurs, offering essentially free resources.
  • Incubators and accelerators provide funding and validation, which can open more doors for startups.
  • Building product-market fit is crucial, and engaging with customers through social media groups, Google form interviews, and polls can provide valuable feedback.

Eppo. Accelerate your experimentation velocity with Eppo. Visit (00:32:01)

  • EPO is an experimentation and feature management platform that centralizes experimentation workflows, enabling faster innovation and better coordination.
  • Grassroots marketing through Facebook groups can help startups connect with their target audience and gather valuable feedback.
  • Analyzing customer interests, behaviors, and product usage can provide insights for product development and marketing strategies.
  • Kelly, a social media video marketer and film producer, turned her idea of reducing mental load into a successful startup.
  • Kelly's success is attributed to her in-depth understanding of her customers and target market.
  • Investors value founders who maintain open communication, even when sharing delays or challenges.
  • Jason Calacanis, the show's host, encourages Kelly to write a book expanding on her insights about the investor side of things.
  • Calacanis believes Kelly's focus on listening to customers and knowing where to find them increases her chances of success.

Francis asks how to strike a balance between skepticism and enthusiasm when evaluating a company for investment, given that it's impossible to invest in every company. (00:39:56)

  • When interacting with founders, it's important to be enthusiastic, understand their vision, and repeat it back to them to build rapport.
  • Instead of focusing on potential problems, investors should look for unique concepts and study past exits in the industry to assess the potential for success.
  • Virality, as seen in LinkedIn's growth, can be a key factor in a company's success.
  • Human psychology plays a significant role in decision-making for both investors and founders, and being well-rested, open-minded, and having a thoughtful process can improve investment outcomes.
  • Optimizing systems and processes is essential for efficiency and effectiveness in investing and other disciplines.
  • Understanding one's own energy levels and preferences can help in designing a process that suits individual strengths and weaknesses.
  • Building a team with complementary skills and strengths is crucial for achieving goals and overcoming challenges.
  • Jason focuses on meeting with founders who have launched their product, acquired customers, and have a few co-founders.
  • Due to time constraints, Jason suggests meeting with a couple of his team members first to gain more information about working with his firm.
  • Building a support team is crucial, and the first hire could be an associate or researcher to assist with deal flow and due diligence.
  • Jason's firm typically makes 8 to 12 investments per year, and having a partner to help organize tasks can make the process more enjoyable.

Hosum asks if explaining their startup's moat as current execution and future benefits after reaching product-market fit is enough to convince investors. (00:52:42)

  • H, co-founder and CEO of Quasi, an autonomous procurement management platform for construction companies, shared key takeaways from Founder University: clearly define the problem being solved, move quickly, and feel comfortable asking questions.
  • Quasi aims to unlock unstructured data in the construction industry to optimize business operations and increase profit margins.
  • Data advantage is a strong moat for Quasi as they accumulate valuable customer data over time, giving them an edge in decision-making and optimization.
  • Investors may use the lack of a moat as an excuse for not investing, but customer feedback is the real test.
  • Offering existing features for free and upselling unique analysis or value-added services can be an effective strategy, as demonstrated by Google's success with Gmail and Google Docs.
  • When choosing a domain name, consider the potential impact on competitors' businesses and how to capitalize on their weaknesses.

Thom asks if not highlighting AI in our funding pitch will hurt our chances of getting investment. (01:02:38)

  • AI is becoming a fundamental technology, making it less unique as a selling point for startups.
  • Investors can differentiate between AI-enabled businesses and those that use AI for specific features.
  • Startups should focus on how AI improves their product, customer support, and future opportunities.
  • AI should be part of a comprehensive strategy that includes operational efficiency, product enhancement, and future AI integration.
  • Investors value thoughtful conversations about business growth, leadership, and handling difficult situations more than an exclusive focus on AI.
  • Startups should use AI discussions to assess potential investors' understanding of their business model and overall intelligence.
  • Founders should be open to listening to advice from smart people in the marketplace.
  • The next episode of "Ask Jason" will be held on the first or second Tuesday of next month during the day. Founders can share the episode with others who might benefit from the content.

Overwhelmed by Endless Content?