Ask Jason LIVE!: Navigating startup growth with Real-Time Q&A | E1937

Ask Jason LIVE!: Navigating startup growth with Real-Time Q&A | E1937

Jason kicks off another Ask Jason with 5 live guests! (00:00:00)

  • Jason introduces the Ask Jason live Q&A session with five guests.
  • He highlights his experience as an investor in 400 startups, founder of multiple companies, host of five podcasts, author of a book, and his extensive knowledge and experience in the startup ecosystem.
  • Vanta simplifies the process of obtaining a SOC 2 report, making it easier for startups to win new business.
  • Twist listeners can get $11,000 off Vanta's services for a limited time by visiting
  • Squarespace allows entrepreneurs to easily create professional websites for their businesses.
  • By visiting, listeners can get a free trial and save 10% on their first website or domain purchase using the offer code TWIST.
  • Mercury provides banking and credit card services specifically designed for startups.
  • With Mercury, startups can join over 100,000 companies and benefit from banking solutions tailored to their unique needs.
  • Interested startups can visit to learn more.

Dustin asks about how to find job opportunities and market his generalist skills (00:01:43)

  • Dustin, a recent startup founder with a technical background, sought advice on marketing his diverse skill set, which includes product design, coding, and operations.
  • Aiming to build financial stability and gain experience from seasoned founders, Dustin had $100K in student debt with a monthly payment of $600 and a personal burn rate of $40,000 annually.
  • Jason suggested co-founding a company instead of building up a cash stack, given Dustin's low burn rate and his successful experience bringing on a co-founder after gaining the first customer.
  • The speaker emphasized the significance of having a strong team rather than being the sole driving force behind a startup's growth.
  • During his entrepreneurial journey, the speaker gained expertise in translating complex products for blue-collar workers and ensuring their successful adoption.
  • Overcoming initial fears, the speaker discovered the joy of building relationships and understanding customer needs through customer interviews.

Vanta - Get $1000 off your SOC 2 (00:09:50)

  • Vanta simplifies the process of obtaining and renewing SOC 2 compliance.
  • SOC 2 compliance is essential for B2B startups that store customer data in the cloud.
  • Vanta can save companies hundreds of hours of work and up to 85% on compliance costs.
  • Vanta automates up to 90% of compliance for GDPR, HIPAA, and more.
  • Hiring the right team is crucial for B2B startup success.
  • Top performers should be given the freedom to excel without being hindered by compliance hurdles.
  • Compliance is essential, but it should not impede sales progress.
  • Vanta offers a solution that streamlines compliance processes, allowing sales teams to close major deals more efficiently.

Dustin asks about how to find job opportunities and market his generalist skills (00:10:42)

  • Dustin suggests building a personal brand around customer discovery, a high-demand skill, and completing a 30-day personal branding challenge to establish expertise.
  • After 30 days, reach out to seed-stage startups and offer consulting services in customer discovery, aiming to engage with 10 startups and secure two clients within two months.
  • Send customized emails to potential clients, spending approximately 15 minutes writing and 1 hour researching each email, and charge a reasonable rate that covers annual expenses.
  • Consider transitioning from consulting to becoming a co-founder of a promising startup if successful.
  • Gradually increase rates as you gain more clients and demonstrate your value.
  • Participate in Founder Fridays in Denver for networking, problem-solving, and potential customer or co-founder connections.
  • Bypass traditional job applications and directly reach out to business owners to secure opportunities.
  • A sniper shot approach, rather than a shotgun or machine gun approach, is more effective in securing opportunities.
  • A 30-day follow-up commitment is expected to review progress and assess the effectiveness of the strategies discussed.

Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain (00:24:57)

  • Squarespace is constantly adding new features and revolutionizing its platform.
  • Squarespace is powered by AI and has a guided design system called Blueprint AI.
  • Blueprint AI helps users build custom websites quickly and easily.
  • Founder University used Blueprint AI to build its website.
  • Blueprint AI tailors everything to the user's preferences, from website structure to color scheme and font pairings.
  • Squarespace offers a free trial and a 10% discount on the first website or domain purchase.
  • Francis Goodluck is an investor and entrepreneur.
  • He has a background in technology and finance.
  • He is passionate about helping startups grow.
  • He is the founder of several successful companies.
  • He is a sought-after speaker and advisor.

Francis asks about defining the terms "likely winner" and "definitive winner" in a strategic framework using specific metrics (00:26:19)

  • A definitive winner in venture capital is a startup with a known VC leading the round, setting the price, originating the term sheet, and joining the board with over 10% ownership.
  • A likely winner is a startup with a priced round, terms coming from the founder, no VC joining the board, and no proper governance.
  • The speaker's investment strategy involves making a small bet in a likely winner and a larger bet in a definitive winner, aiming for 10-15% ownership in definitive winners.
  • Jason recommends fund managers to have a larger amount of reserves, around 40%, for better investment strategies. He suggests investing 50k in 100 names and then taking 5 million to invest 500k into the top 10 performers.
  • Early-stage startups typically have around 25 to 50 unique investors on their cap table by the time they reach Series A funding.
  • Francis, an audience member, shares that he invests using Jason's strategy, adapted to a smaller scale, with 50% reserves.
  • Jason mentions Angel University, a three to four-hour class for $300, where all proceeds go to charity.

Mercury - Join 100K+ startups banking with Mercury (00:39:15)

  • Mercury is a banking platform designed for startups.
  • It offers simplified banking and finance operations.
  • Complete banking tasks in just a few clicks.
  • Streamline operations with real-time data from your bank account.
  • Explore all the tools and how it works with Mercury's interactive demo.
  • Pay bills faster, control company spend, and speed up reconciliation.
  • Gain precision control and focus needed to transform operations.
  • Over 100,000 startups trust Mercury for financial excellence, growth, and community.
  • Apply in minutes at and start transforming your startup's journey.

Mathew asks about choosing between mission-aligned sponsors and more lucrative, unrelated advertising opportunities for his podcast (00:40:17)

  • When choosing sponsorships, consider the alignment between the sponsor's product and the podcast's niche, as well as the potential reach and return on investment.
  • Underpricing ads and overdelivering value can create long-term relationships with sponsors, while being selective about sponsors helps maintain the podcast's credibility.
  • Podcast advertising ROI should be viewed as a combination of brand building and direct ROI, with value derived from influencer endorsements and general awareness.
  • Understand your podcast's natural audience and target sponsors accordingly, considering additional offerings like newsletters or in-person meetups to provide more value.
  • Focus on creating valuable content and connecting with your audience, especially the top 1% of listeners, through email marketing and direct relationship building.
  • Sound quality is crucial for a successful podcast.

Jason asks whether to continue low-cost growth strategies or seek seed funding to boost growth through advertising, as their product is the advertising itself (00:52:23)

  • JD, the founder of a marketing and advertising startup for independent gyms, is considering whether to focus on low-cost growth or raise a seed round for accelerated growth.
  • Their network marketplace offers world-class marketing and advertising services, with a three-tiered pricing plan and 10 satisfied customers.
  • To scale and attract venture capitalists, the business needs to transform from an arbitrage-style agency into a software platform accessible to anyone.
  • The key decision is to determine the best-fit customer base and consider a different category with a higher ticket price.
  • Experimentation and triangulation are crucial to identify significant arbitrage opportunities and validate the business's potential.
  • Venture capitalists are interested in platform-based businesses with a clear beachhead market, sustainable growth, and the potential for high margins and innovation.
  • The business should evolve into a platform where users can participate without salespeople, similar to successful platforms like HubSpot or YouTube.
  • A top-down approach is needed to fix consistency issues in a highly fragmented market.
  • As the market and product grow, revenue from multiple markets can be applied to a single national campaign.
  • Additional products can be added once the chasm rules are followed and the fragmented market is fixed.

Douglas asks about how a non-AI startup with traction can stand out to potential investors (01:04:05)

  • The startup offers premium experiences and revenue models for independent brick-and-mortar businesses through membership programs and subscriptions.
  • It has 31 paying customers and a letter of intent from another dozen.
  • The top 15 customers generate an average revenue of $900 per month, with the startup capturing $10,000 per customer.
  • A successful customer, a restaurant, introduced a $100 membership fee for priority seating and other perks, attracting 17 recurring customers and generating $1,700 monthly revenue, potentially covering 30% of its $5,000 monthly rent.
  • The business model doesn't involve AI and may not attract significant VC interest, but its growth, customer feedback, and churn rate will be crucial metrics for evaluation.
  • The owner should consider incubator/accelerator programs or a seed round to scale up.
  • Customer discovery expanded from restaurants and bars to various establishments based on demand, and focusing on owners familiar with subscription models proved effective.
  • Membership clubs can be successful by offering exclusive benefits and perks that appeal to customers.
  • An extroverted and passionate person who can engage with local businesses and build relationships is crucial for growth.
  • The founder should reach out to the Founder University team or the launch accelerator team to explore opportunities.

Founder Fridays! (01:15:37)

  • Founder Fridays is an opportunity for founders to meet and discuss their experiences, challenges, and successes.
  • It's a chance to network with other founders and learn from each other.
  • Founder Fridays are held on the first Friday of every month in 71 cities around the world.
  • Founders can sign up to attend or apply to run a Founder Friday in their city.
  • The next Founder Friday is on May 3rd, and the prompt is to bring two things: your most significant challenge and one thing you wish you'd learned earlier.
  • Sign up at to attend a Founder Friday.
  • Take pictures and share them on Twitter at @jason and @twi_startups.
  • Founder Fridays are happening in 71 cities worldwide, with over 900 members.
  • The goal is to reach 100 cities and 1,000 members.

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