Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

  • 15 minutes 20 seconds
    Episode 763 | TinySeed Tales s4e8: One Last Pivot

    Is it time to set a deadline for when to quit your startup?

    In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hello Query, as she tries to achieve product-market fit on a deadline.

    Colleen reveals the struggles of cold outreach and the overwhelming data landscape while testing a potential solution. With a clearer vision and two paying customers, she reflects on the importance of defining her value proposition, and the critical timeline she has set for herself to gain traction before her runway ends.

    Topics we cover: 

    • (1:43) – Debating becoming a data aggregator 
    • (6:30) – Finding a new direction
    • (8:21) – Running out of runway
    • (10:39) – When is it time to quit?

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    6 March 2025, 10:00 am
  • 25 minutes 5 seconds
    Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

    Are public deadlines a double-edged sword for startup founders?

    In episode 762, join Rob Walling for a solo adventure where he covers several topics. Rob breaks down Paul Graham's essay, "Doing Great Work" and focuses on how the steps apply to building real businesses for real customers. He also discusses the hierarchy of skills necessary for success in the SaaS space, sharing his thoughts on the critical roles of marketing, product development, engineering, and effective team management.

    Topics we cover: 

    • (2:07) Doing great work
    • (5:20) Identify the gaps
    • (11:51) The SaaS skillset hierarchy
    • (18:28) Publicly committing to a feature release
    • (23:05) Maintaining enough rigor to hit deadlines

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    4 March 2025, 10:00 am
  • 20 minutes 34 seconds
    Episode 761 | TinySeed Tales s4e7: Identifying Pain Points

    In this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she discusses finding customer pain points.

    Colleen, now solo, navigates the challenge of refining her product vision. After a period of introspection, Colleen shares her decision to pivot from targeting engineering managers to focusing on marketing data analysts. She discusses the insights gained from hiring a marketing coach and the excitement of landing her first paying customer, despite some critical feedback on her product's UI.

    Topics we cover: 

    • (1:50) – Early product excitement fizzles out
    • (5:14) – When is it time to move on from an idea?
    • (8:57) – Helping marketers build better reports
    • (13:03) – Setting early pricing
    • (14:02) – Determining how much to polish an MVP
    • (17:36) – Predicting what’s ahead

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    27 February 2025, 10:00 am
  • 32 minutes 38 seconds
    Episode 760 | White-Labeling, Founder Mindset, and More Listener Questions (A Rob Solo Adventure)

    In episode 760, join Rob Walling as he takes on some listener questions in another solo adventure. He offers insights on balancing custom-built solutions versus white-labeled components, and the impact white labeling has on company valuation and growth. He also discusses strategic hiring, founder mindsets, and tools for tracking your SaaS success.

    Topics we cover: 

    • (2:30) – Considerations when white-labeling within your SaaS
    • (9:03) – Does relying on other SaaS affect our valuation?
    • (10:10) – Tools for tracking SaaS metrics to enable scaling
    • (17:03) – Do founder mindsets change at MRR milestones?
    • (21:34) – Mistakes founders make in their mindset
    • (25:27) – Forcing an onboarding step
    • (27:29) – Determining team composition

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    25 February 2025, 10:00 am
  • 27 minutes 10 seconds
    Episode 759 | TinySeed Tales s4e6: Does AI + Pivot = Success?

    In this episode of TinySeed Tales, Rob Walling speaks with Colleen Schnettler, co-founder of Hello Query, as she shares her latest startup journey pivot.

    After reigniting her “shipping muscle” while briefly dabbling in an AI-based project, Colleen refocuses on her newest pivot of Hello Query. She shares the challenges of determining the market viability of an AI-assisted SQL report builder. She stands at a crossroads, torn between catering to internal BI teams or exploring marketing analytics.

    Topics we cover: 

    • (1:25) – Reflecting on the co-founder breakup
    • (2:42) – Trying a scratch-your-own-itch project
    • (6:27) – Unfair advantages inform another pivot
    • (15:07) – Respecting the “emotional runway”  
    • (19:23) – Marketing insights vs. an internal BI tool
    • (23:01) – The curse of the audience

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    20 February 2025, 10:00 am
  • 45 minutes 9 seconds
    Episode 758 | Do Free Trials Suck?, What Moves the Needle, and More Listener Questions (with Derrick Reimer)

    In episode 758, Rob Walling is joined by Derrick Reimer to tackle a variety of listener questions. They discuss strategies for entering a market with established competitors, including how to position your product without directly attacking rivals. They also reflect on the challenges of free trials, weighing the pros and cons of extending trial periods versus incentivizing onboarding.

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    Topics we cover: 

    • (1:18) – How to launch a SaaS product in a market with an established competitor
    • (6:21) – Do I call out competitors by name?
    • (14:24) – How do you really identify what moves the needle in your Saas?
    • (19:59) – Breaking down the “one thing”
    • (23:32) – Selling and marketing SaaS before building
    • (30:36) – What is the goal of your free trial?
    • (39:10) – On the fence between B2B, B2C

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    18 February 2025, 10:00 am
  • 15 minutes 24 seconds
    Episode 757 | TinySeed Tales s4e5: Founder Breakups, Crushing Failures, and the Future

    In this episode of TinySeed Tales, Rob Walling chats with Colleen Schnettler, co-founder of Hello Query, as she navigates the complexities of her startup journey. 

    After a challenging period with her co-founder Aaron, Colleen reflects on their decision to part ways and the emotional toll it has taken on her. She shares her feelings of crushing failure, the uncertainty of moving forward alone, and the realization that their initial product vision may not align with market needs. 

    Topics we cover: 

    • (0:49) – Colleen and Aaron make a tough decision
    • (4:09) – Voice memo, “Crushing Failure”
    • (7:59) – What if you hadn’t raised money?
    • (11:44)  – Colleen weighs her remaining options

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    13 February 2025, 10:00 am
  • 43 minutes 10 seconds
    Episode 756 | Why Great Product Management Is Critical for Your Startup

    In episode 756, Rob Walling interviews Brendan Fortune, Director of Product Management at Customer.io, to explore the skills and frameworks for effective product management. Brendan shares his journey and discusses the importance of understanding customer behavior to drive product decisions. They delve into the concept of the flywheel and how it can be leveraged to enhance user success and optimize pricing strategies.

    Topics we cover: 

    • (2:46) – What does a product manager do?
    • (10:36) – When should a SaaS company designate a full time product manager?
    • (15:33) – Pricing and and creating a flywheel
    • (22:41) – Deciding on your “fair” value metric
    • (30:01) – Pricing experimentation in the early days

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    11 February 2025, 10:00 am
  • 15 minutes 47 seconds
    Episode 755 | TinySeed Tales s4e4: Customer Interviews + Pivoting

    In this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she shares the latest developments in her startup journey. 

    Colleen shares the insights gained from recent customer interviews that led to a significant pivot in their product strategy. Hello Query is now focused on embedding custom reporting features within other SaaS applications and Colleen reflects on balancing product quality with minimal v1 features. Her excitement is building to get their solution into users' hands.

    Topics we cover: 

    • (1:32) – Digging into customer interviews
    • (3:54) – Filtering out the noise to achieve confidence
    • (5:31) – Other competitors in the space
    • (8:53) – How Colleen prepares for and sources customer conversations
    • (12:11) – Is the technical implementation coming along?

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    6 February 2025, 10:00 am
  • 25 minutes 22 seconds
    Episode 754 | Broken Freemium, SaaS Plateaus, and More Listener Questions (A Rob Solo Adventure)

    In episode 754, join Rob Walling for a solo adventure as he tackles listener questions on a variety of topics. He discusses strategies for converting free users to paid customers, the implications of AI advancements on the SaaS landscape, and how to navigate platform risks when larger players enter your market. Rob also shares insights on breaking through growth plateaus.

    Topics we cover: 

    • (3:12) – When in doubt, don’t try freemium
    • (6:44) – Different levers you can pull to make freemium work
    • (8:53) – How will SaaS be affected by the exponential growth of AI?
    • (14:09) – Big players launching features is a form of platform risk
    • (17:24) – Should I spin out a portion of my product into a new product?
    • (20:05) – Thinking through plateaus in your business growth

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    4 February 2025, 10:00 am
  • 23 minutes 10 seconds
    Episode 753 | TinySeed Tales s4e3: Co-Founder Conflicts + Renaming a Business

    In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hammerstone, as she shares the latest developments in their startup journey.

    Colleen opens up about the emotional challenges of co-founder conflicts with Aaron, highlighting the importance of communication and alignment in their partnership. They also discuss the significant pivot from their initial product offering to the newly rebranded Hello Query, a SaaS solution focused on internal reporting for teams.

    Topics we cover: 

    • (0:59) – Breaking up with a co-founder
    • (7:39) – How could this conversation have been different?
    • (9:49) – Navigating a major pivot
    • (14:37) – Changing the name
    • (16:56) – Getting closer to finding product-market-fit
    • (19:39) – Competing in a competitive market

    Links from the Show: 

    If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

    Subscribe & Review: iTunes | Spotify

    30 January 2025, 10:00 am
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