Title: $0 to $3M ARR in 21 Months, with Order Editing’s Hamish McKay
Session context
Format: Fireside talk + Q&A (no slides)
Host: Louisa (Startmate)
Speaker: Hamish McKay (Founder/CEO, Order Editing; bootstrapped from $0 → ~$3M ARR in ~21 months; team of ~10; Shopify ecosystem)
https://www.linkedin.com/in/hamish-mckay/ Model: B2B SaaS for Shopify brands; enables shoppers to edit orders post-purchase; pricing ~$40–$3,000 USD/mo
Founder profile: Non-technical commercial founder; technical co-founder found via Twitter; remote-first; heavy on strategy, distribution, and founder-brand
Core narrative: reverse-engineer outcomes, then execute
Five-year lens beats one-year sprints: stack habits, compound skills, and network; “people overestimate 12 months, underestimate 5 years”
Define your dream outcome before building: lifestyle vs scale vs quick, de-risked exit; pick a path you’ll sustain
Reverse-engineering: choose a target (e.g., $1M ARR in 12 months), derive the fewest needle-movers, ignore the rest
Playbook: Year 1 to Year 3 strategy
Year Target and thesis Core levers (only 3) Notes Y1 0 → ~$1M ARR fast; credibility and virality 1) Founder-led distribution on LinkedIn; 2) Win marquee fashion brands for K-factor; 3) Trade small equity for influencer/operators’ distribution Avoid partnerships that need scale (e.g., large platforms) and high-friction cold-only motion Y2 Triple to ~$2.5–3M ARR Keep compounding organic; systemize sales; maintain velocity; tighten ops Hit ~30 closed-won/month at ~$5k ACV (ARR) Y3 Triple again to ~$7.5M ARR (plan) 1) Increase ARPU (e.g., $5k → $10k); 2) Build account management/upsell muscle; 3) Ship upsellable product modules ARPU doubling reduces required deal volume vs scaling headcount-heavy sales
Founder-led distribution and equity-for-distribution
Motion How it worked Outcome/metric LinkedIn build-in-public Daily posts; founder story; transparent milestones; ICP lives on LinkedIn Inbound leads; affinity → lower churn/ higher social proof Category beachhead: fashion Consumers buy fashion often → see Order Editing in the wild → e-comm operators notice ~10%+ revenue via “saw it in checkout” K-factor Equity to influencers/operators ~3.5% equity to strategic angels with large reach; targeted intros and social amplification ≈$300k ARR directly; favorable “girl math” on value vs dilution
Early-stage execution principles
Principle Why it matters Practical example Do the obvious consistently Habits compound: reading, grades, mentors, reps in communication/sales 100 books in 2 years; straight A’s; relentless outreach Strategy = subtraction Pick the top 3 levers; ignore everything else Kill “big partnership” dreams until you have scale Build while employed De-risk: MVP built with contractor; quit when first dollars arrive First $ in Dec ’23; full-time Jan ’24 Hire to your gaps Tech via co-founder/contract; later AMs for upsell Non-technical founder focuses on distribution, product narrative, strategy Track everyone, forever Never lose a warm contact HubSpot + VA creates follow-up tasks for every email/meeting
Tactical systems Hamish uses
Area System/Tooling Details CRM HubSpot + VA Every interaction → follow-up task; 2 hours/day inbox triage; zero lead leakage Meetings High volume (historically ~30 hrs/week) Thousands of contacts/year → strict tasking cadence Sales Founder-led; clear ICP; simple funnel Avg deal ≈ $5k ARR; ~30 deals/mo Product Narrow wedge solving obvious CX pain Strong ROI case for brands; upsell opportunity via modules/integrations Content LinkedIn first Affinity + credibility = better conversion and retention
Strategy cadence and “thinking time”
Practice How Hamish does it Strategy docs Write structured memos: where we are → why now → constraints → options → chosen plan; share internally Cadence Early: monthly; now: ~quarterly or ad hoc when decisions bottleneck execution Peer/mentor loop Draft → second-in-command review → team; maintain a public internal archive for new hires Reframe Start with wins to reduce stress bias; then tackle thorns logically
Benchmarks and pacing
Stage Indicative pacing From $0 to first dollars Contractor-built MVP; sell before perfect; leave job after initial revenue Y1 volume ~30 closed deals/month at ~5k ACV Y3 arithmetic To add $5M ARR: either 80 deals/mo at 5k ACV or fewer deals at ~10k ACV Chosen lever Prioritize ARPU growth + AM-driven upsell to reduce headcount/sales pressure
Selected Q&A highlights
Topic Takeaway 12 months vs 5 years Five years lets habits, skills, and networks compound; set audacious 5-year goals, not shallow 12-month ones Finding distribution partners Don’t ask for “networking”; ask one valuable, specific question; follow up with updates; water relationships Strategic equity Offer small equity to operators/influencers with true reach in your ICP; measure ARR impact Thinking ritual Ad hoc deep dives when overwhelmed; structured memo; externalize, review, ship Mentors Different mentors for different phases: skill gaps (sales) and founder-strategy veterans Project management Simple funnel worldview; CRM rigor beats PM complexity early Work while building Build POC/MVP alongside job; flip to full-time once revenue lands
8-week execution template (fill this in)
Track Baseline (now) 2-week goal Weekly target Success criteria Distribution LinkedIn cadence + ICP list 10 posts; 50 ICP connects; 10 warm replies 2 posts, 25 connects, 5 DMs/day 10 meetings/week; reply rate ≥ 20% Pipeline Leads in CRM Zero leakage: tasks for 100% of leads Daily CRM hygiene; VA 2h/day 100% follow-up within 72h Deals Current close rate, ACV Close 10 new at current ACV 20 pitches/week Close rate ≥ 30–50% (fit-dependent) ARPU Current pricing/packaging Draft upsellable module + pricing test 5 upsell calls/week ARPU +20–50%; 3 pilot upgrades AM/upsell No dedicated function Hire/assign AM; define playbook 10 QBRs/week (light) Expansion revenue ≥ new-logo revenue (target path)
Practical metrics you can choose
Acquisition: meetings/week; response rate; inbound vs outbound mix
Conversion: close rate; sales cycle length; ACV/ARPU; payback
Expansion: net revenue retention; expansion vs contraction dollars; QBR completion rate
Retention/love: logo retention; “very disappointed if removed” %, case studies, public reviews
Ops: lead leakage (should be 0); time-to-first-response; follow-up SLA compliance
Workshop logistics and follow-ups
Item Details Strategy book Shared by Hamish in Zoom chat (to be posted on recordings page) Connect LinkedIn: follow Hamish; he builds in public and shares updates Tools referenced HubSpot (CRM), VA support, LinkedIn, Stripe/Shopify context Recording/notes Session recording and links to be shared to cohort
Define your 3 levers for the next 12 months; cut everything else
Stand-up CRM hygiene: every contact gets a follow-up task; hire a part-time VA if needed
Post founder-led content 2–3x; target 25 ICP connects/day; book 10+ meetings
Choose a beachhead category with K-factor potential; pursue 3 logos
Draft one upsellable module and a pilot price; schedule 5 upsell conversations with current customers