Olly Meakings

Olly Meakings

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Senja cofounder; maker marketing and founder distribution experiments.

Paid Trial Weeks: Avoid Asking Employed Candidates to Use Vacation
SocialApr 30, 2026

Paid Trial Weeks: Avoid Asking Employed Candidates to Use Vacation

I always offer candidates a paid one week trial This is easy if they’re working freelance or between jobs But if they’re currently employed, is it reasonable to suggest they use holiday time?

By Olly Meakings
When Success Feels Stagnant, Lifestyle May Be Enough
SocialApr 29, 2026

When Success Feels Stagnant, Lifestyle May Be Enough

My SaaS revenue and sign ups are flat I'm plateau-d at $1,000,000 a year A great achievement but a challenging spot to be in According to @robwalling only 5% of bootstrapped startups escape these types of revenue plateau The more complicated issue is that...

By Olly Meakings
X Is a Launchpad, Not a Retention Strategy
SocialApr 23, 2026

X Is a Launchpad, Not a Retention Strategy

#buildinpublic is fast food marketing Quick sign ups, high churn There are a lot of smart people marketing their SaaS exclusively on X And they all have one thing in common - disastrously high churn of >20% a month These founders have to replace...

By Olly Meakings
New Role Switcher Makes Product Shipping 100x Faster
SocialApr 20, 2026

New Role Switcher Makes Product Shipping 100x Faster

We just made shipping a great product 100x easier @ngrushkovsky just shipped a plan / role switcher I can quickly impersonate any account on any tier with any role Ideal for quickly reviewing paywalls and feature access #buildinpublic https://t.co/rQaGV92TGl

By Olly Meakings
Revenue Stalls Even as Customers Grow, Churn Matches Upgrades
SocialApr 16, 2026

Revenue Stalls Even as Customers Grow, Churn Matches Upgrades

Our revenue at Senja has plateaued We're up 40% in the last 365 days But month on month growth is basically 0 As our customer number increased, our churn and upgrades have met (about 10 a day) Now what? #buildinpublic https://t.co/FY16xbozbp

By Olly Meakings
Request for Stripe‑style REST API to Manage Webhooks
SocialApr 16, 2026

Request for Stripe‑style REST API to Manage Webhooks

@MuxHQ Can we get REST endpoints like Stripe's POST /v1/webhook_endpoints to programmatically create/delete per-environment webhook URLs?

By Olly Meakings
Bootstrappers Meet Up in Vancouver for a Few Weeks
SocialApr 16, 2026

Bootstrappers Meet Up in Vancouver for a Few Weeks

Who's in Vancouver? I'm going to spend a few weeks in this beautiful city Any bootstrappers around and want to hang out?

By Olly Meakings
AI Bug‑Fix Pipeline Nears Launch, Integrates Top Tools
SocialApr 11, 2026

AI Bug‑Fix Pipeline Nears Launch, Integrates Top Tools

🤏 We're this close to launching our AI bug fixing pipeline It gracefully connects @linear @jamdotdev @claudeai @sentry and @greptile https://t.co/RGEJWqunwR

By Olly Meakings
AI Speeds Content, but Makes Marketing Tougher
SocialApr 9, 2026

AI Speeds Content, but Makes Marketing Tougher

AI makes marketing harder not easier Yes, you can produce marketing and sales content at 10x the speed But so can everyone else

By Olly Meakings
Founders Who Monetize AI-Driven Marketing Lead Revenue Growth
SocialApr 8, 2026

Founders Who Monetize AI-Driven Marketing Lead Revenue Growth

Who's making more money with AI? Not people selling spades, but existing founders shipping more marketing work that's driving revenue? I see lots of founders running more experiments, trying new things, and saving time. But who can attribute extra revenue to work delivered...

By Olly Meakings
Lifecycle Emails Drive Monthly-to-Annual Subscription Upgrades
SocialApr 8, 2026

Lifecycle Emails Drive Monthly-to-Annual Subscription Upgrades

We now send our users multiple emails... When they sign up When they upgrade When they churn To turn monthly subscriptions into annual What next?

By Olly Meakings
5‑Week Sprint Cycle Boosts Team Energy and Metrics
SocialApr 7, 2026

5‑Week Sprint Cycle Boosts Team Energy and Metrics

I’ve just kicked off a 5 week cycle with new engineer Each cycle has 5 sprints Each sprint contains one feature or product change based on metrics, a series of papercut fixes, and bug fixes. Sprint 5 is a cool down with...

By Olly Meakings
Financial Security Resets Motivation, Lets Bootstrappers Choose Growth
SocialApr 4, 2026

Financial Security Resets Motivation, Lets Bootstrappers Choose Growth

This is true for me I used to be confused why bootstrappers slowed down after hitting revenue milestones like $20,000 a month But I realised that for most of them, they have enough 6-10 months of having 'enough' is a real reset in...

By Olly Meakings
AI‑Driven Roadmap: Blend Data, Feedback, and Bets
SocialApr 3, 2026

AI‑Driven Roadmap: Blend Data, Feedback, and Bets

How do I plan a product roadmap in 2026? I haven't done it in a year as we've been firefighting I want to combine customer requests, insights from support, customer adoption data, fun stuff, and bets What's the playbook in 2026? Connect everything to...

By Olly Meakings