Why Going Up Market Too Early Kills Startups | Why New Categories Cannot Do Traditional Sales | Why "Sell to Pain" is Terrible Advice for New Categories | The Hidden Truth About Box, Asana & HubSpot's Growth | Matt Harmon, GTM Advisor & Former Box/Asana

Moving upmarket, the right wayWhen should a startup go from SMB to enterprise - and when should you not?I break this down with a former revenue leader at Box, SurveyMonkey, Asana, etc - Matt Harmon (ex‑Box, Asana, SurveyMonkey). We discuss the real signals for enterprise readiness, why security/compliance readiness matters, and why “we’ll build it if you buy it” kills confidence. We also compare playbooks for existing vs. new categories, the land→expand reality, and how to balance self‑serve revenue with enterprise ambitions.In Today's Episode We Discuss:1:42 Why the “go upmarket” conversation starts early4:53 Company readiness: security, compliance, SEs, forecasting shifts10:57 Signals it’s curiosity-only vs. a real enterprise opportunity16:45 “Is it someone’s KPI?” and the need for true pain/need18:36 Existing category = one path to buy (ripping/replacing)22:52 New category upmarket: shared services & proving uniqueness28:28 Land→expand and product-led reality33:08 Don’t force a model—map the customer journey first37:57 Positioning and intellectual honesty at ~$1M ARR40:00 Category creation vs. innovating in an existing one45:07 Why not to fear SMB/self-serve revenue47:15 Don’t over-index on “sell to pain” for new categories50:15 Founder advice: embrace ambiguity and EQ52:25 What great VCs do: back leaders who can hire leaders