Summary of 20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

Overview of 20VC: Raising $400M for 20VC (Simon Squibb Edition)

This episode flips the usual 20VC format: Simon Squibb interviews Harry Stebbings. They go behind the scenes of 20VC, Harry’s fundraising approach for a $400M fund, how he landed Marc Benioff after 53 cold emails, and seven distilled lessons from interviewing 101 decacorn founders. The conversation mixes tactical fundraising and sales playbooks with career and life lessons for founders and early-stage operators.

Key themes covered

• How to raise (and sell) at scale: cold outbound, social proof, persistence, and moving conversations off email.
• Media as a distribution engine for venture and startups — creator-as-platform thinking.
• Practical, high-leverage habits for founders: hiring fast, showing up, iterating content, and prioritising relationships.
• The emotional and human side of success: what actually makes you happy, the role of family, and how to build durable momentum.

Notable anecdotes & stories

• 19-year-old Harry raised £1.75M in 24 hours by emailing 25 CEOs with a contrived sponsorship pitch and leveraging urgency/FOMO (priced just under £100k procurement thresholds).
• Harry raised £70M via WhatsApp by privately messaging high-net-worth individuals during breaks at the gym — after 10 years of relationship building.
• Harry emailed Marc Benioff 53 times (each email with fresh personalization and a new P.S.) before getting a “yes.”
• Both hosts emphasise long, uneven early streaks in media: the first 3–4 years often show almost no traction.

The 7 lessons from 101 decacorn founders (concise)

1. Never accept “no” as final

   • Push back, re-open conversations and call. Accepting immediate rejection leaves money and opportunities on the table.

2. Beat down the door (persistence + personalization)

   • Persistent, high-quality cold outreach works (example: 53 emails to Marc Benioff). Each follow-up should add a fresh personal detail.

3. Start before you’re ready

   • Activity drives outcomes. Most people fail to start because they fear failure; iterate publicly and learn fast.

4. Use role-model decision frameworks

   • When stuck, ask “What would X (someone you respect) do?” as a short-circuit for better, principled choices.

5. Don’t chase money for its own sake

   • Money solves many problems, but chasing it alone rarely leads to fulfilment. Find the “$5.60” moments (small things that truly make you happy).

6. Break big visions into small, achievable milestones

   • Ambitious missions are won by compiling short-term wins; focus on the next milestone, not the entire summit.

7. Influence the influencers (and be nice)

   • People’s partners, chauffeurs, assistants and “car-ride home” conversations often decide outcomes. Be polite and win the people around your target.

Practical fundraising & sales tactics

• Cold outreach formula: short, personal, clear ask + social proof. End with a highly personalized P.S. (e.g., shared hobbies/whiskey).
• Cadence: persistent weekly follow-ups (add value or personalization each time).
• Social proof flywheel: each high-profile guest helps recruit the next — ask guests for 3 introductions and for a forwardable intro email.
• Move conversations off email to WhatsApp/phone to build rapport and relationship currency.
• Mitigate risk before quitting: secure at least one customer or sponsor, then burn the boats if necessary.

Media, distribution & creator-as-platform insights

• Distribution is the primary differentiator: creators can become platforms and launch products that previously were promoted by others.
• Build distribution early — one viral/consistent post can unlock revenue and deal flow.
• Content is a form of scalable mentorship: people follow creators as if they were mentors; you can pre-sell trust at scale.
• Iterate hooks and formats quickly (short-form + long-form combo), and treat production/process details as defensibility.

Career & life advice for young founders

• Chase your first million aggressively — it unlocks options and access (but don’t fetishize money).
• University is overrated for many; early risk-taking is easier when young.
• Hire quickly for accountability — a team forces follow-through.
• Work harder than your peers if you have the time; persistence beats talent in early stages.
• Keep a “two-hob” approach: you can realistically maintain two of four priorities (family, friends, work, fitness); find clever ways to combine them.

Habits & small rituals that matter

• Build daily micro-relationships: learn the names of the two people you see most (barista, receptionist).
• Share personal content (e.g., posts about family) — it humanises you and builds deep audience engagement.
• If decisions are hard, use a model mentor (real or via content) to guide choices.
• Combine activities: exercise + work calls, family in the company, team-at-gym, etc.

Actionable to-dos (quick checklist)

• If fundraising or pitching: craft a short, 1–2 sentence ask; include a personalized P.S.; follow up weekly with new personalization or value.
• Convert email threads to WhatsApp/phone for relationship building after the first good call.
• Start content today: produce and iterate (one TikTok/day or a weekly podcast episode).
• Hire one person ASAP when starting something — accountability speeds results.
• Pick two daily contacts (names) and build those small, high-frequency relationships.
• For big goals: define the next milestone and work only on that until achieved.

Notable quotes

• “If you want to win, be a purple cow.” — Harry Stebbings
• “Distribution is everything.” — Discussion takeaway
• “The details are not the details. They are the product.” — Gustav Söderström (quoted)
• “If you have the ability to be miserable for no reason, you have the ability to be excited for no reason.” — Harry Stebbings

Sponsors & resources mentioned

• Perk (travel & spend automation)
• Daily Body Coach (health coaching for execs)
• Airwallex (global payments & treasury)

Summary verdict: high-value episode for founders, VCs, and creators. It mixes tactical outreach and fundraising playbooks with mindset, process, and content-distribution strategies — all illustrated with concrete stories (the £1.75M sponsorship stunt, WhatsApp fundraises, and the 53-email persistence to Marc Benioff).