Choosing between AI projects, niche marketing, pricing, and more

Executive overview

Solo founders face recurring decisions: which idea to pursue, how narrowly to market, when to cut prices, and how many customer profiles to target. Rob Walling answers five listener questions, drawing on patterns from 200+ Tiny Seed investments.

Good frameworks beat gut reactions — but gut reactions informed by pattern-recognition beat paralysis.

Early positioning is a bet you can undo; not starting is a bet you can't.

Choosing between two side projects

• Regulatory hurdles as a solo bootstrapper are a serious drag on velocity — not a reason to kill an idea, but a reason to deprioritise it.
• Passion projects can be mothballed, not abandoned — hack on them when burned out from the main project.
• Finding a competitor's Achilles' heel (bad reviews on Capterra/G2, missing features, poor pricing model) is a legitimate path into a crowded market.
• Use the 5PM Framework to evaluate ideas systematically rather than relying on anyone else's gut read, including the host's.
• No adviser can reliably predict which idea will work; they can only flag obvious structural problems.

Early niche marketing and pigeonholing

• Niching into a specific segment early does not permanently constrain the product — it accelerates traction.
• Expansion is a marketing execution problem, not a brand identity problem: re-architect the site, bang social media drums, and announce a new positioning milestone.
• ConvertKit (now Kit) moved from authors → bloggers → creators; BidSketch moved from designers → anyone needing proposals; Intercom moved from a single chat widget to a broad suite.
• HubSpot started as inbound marketing landing pages and became a dominant CRM — nobody thinks "pigeonhole" now.
• The play: start narrow, gain traction, then expand deliberately with a clear announcement.

When to lower prices

• Lowering prices is warranted when: customers consistently don't value the quality differential, competitors undercut on the feature that matters most to buyers, or external shocks hit the customer base (layoffs, spending freezes).
• Venture-funded land grabs are a legitimate reason to drop prices aggressively — but only with capital to sustain the burn.
• The default error is underpricing, not overpricing: ~75–80% of early-stage founders arriving at Tiny Seed have pricing that's too low, value metrics that are off, or missing tiers.
• Common mistakes: flat monthly pricing with unlimited usage, no enterprise plan, failing to charge large customers proportionally more.
• Of 100+ Tiny Seed companies that raised prices, only one or two saw it backfire. Most regret not raising sooner.
• Blanket advice ("always raise prices") has real exceptions; the signal to lower is persistent deal loss where quality differentiation isn't converting.

One ICP versus multiple ICPs

• ICP (ideal customer profile) = the specific role, company size, and vertical you target.
• One ICP is simpler and forces sharper positioning; multiple ICPs hedge the bet but spread resources thin.
• If three ICPs are adjacent (e.g. lawyers, accountants, mortgage brokers), the trade-off is milder — a slightly weaker H1 versus learning which vertical takes off.
• Orthogonal SaaS: targeting a specific job title across company types — a hybrid between vertical (industry niche) and horizontal (any company).
• Keep branding flexible from the start: avoid vertical-specific domain names, colours, or design that would require a rebrand to expand.
• The right question before committing: what data can I gather now to confirm or deny which ICP is the right bet?

Building for the Slack App Store with new install requirements

• Slack raised its submission bar: 10 workspace installs required before app review.
• This is a minor hurdle, not a reason to abandon the project — getting 10 installs takes days via warm outreach, not months.
• Tactics: post in MicroConf Connect, IndieHackers, private Slack channels, Twitter/LinkedIn — ask directly for test installs.
• Tiny Seed companies routinely crowdsource the required Zapier installs the same way; it's standard practice.
• A higher install bar is a mild moat — it filters out low-effort competing apps.
• Do not rebuild for a different app store; work the network and clear the bar.