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Cashflow Blueprints

Persistence Pays Off: How a 29-Year-Old VC Founder Turned 53 Cold Emails into a Cashflow Breakthrough with Marc Benioff!

Last updated: February 6, 2026 8:51 pm
Muxudo
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Contents
  • Step 1: Craft a Compelling Subject Line
  • Step 2: Get to the Point
  • Step 3: Validate Your Proposal
  • Step 4: Specify Time Commitment
  • Step 5: Personalize Your Message
  • Step 6: Do Your Homework
  • Step 7: Act Quickly After Meetings
  • Step 8: Be Persistent
  • Conclusion: Open New Doors

Step-by-Step Blueprint for Successful Cold Emailing

Harry Stebbings, the founder of the venture capital firm 20VC, exemplifies the art of persistence in cold emailing. His experience in landing high-profile guests, like Marc Benioff, CEO of Salesforce, offers a solid strategy for making meaningful connections and improving business opportunities. Here’s a structured approach based on his techniques.

Step 1: Craft a Compelling Subject Line

Begin with a subject line that grabs attention but doesn’t come across as needy. Avoid generic phrases; instead, aim for clarity and intrigue.

Step 2: Get to the Point

In your opening lines, skip the filler. Instead of saying, “‘I hope you’re well,'” dive straight into your objective. Make it clear why you’re reaching out right after your salutations.

Step 3: Validate Your Proposal

Support your request with credibility. Briefly outline your background, including key statistics that demonstrate your value. “We have X amount of subscribers, followers, etc., and I’ve had guests like X, Y, and Z,” is a great format to use.

Step 4: Specify Time Commitment

Let your recipient know how much of their time will be required. This transparency helps set expectations and showcases your respect for their schedule.

Step 5: Personalize Your Message

Wrap up your email with a personal touch. Stebbings tried various options for his outreach to Benioff, such as offering a favorite whiskey or drawing attention to a shared interest. Find something relatable in your recipient’s background or interests.

Step 6: Do Your Homework

Utilize AI tools and large language models (LLMs) to uncover unique, lesser-known facts about your recipient. This shows that you are genuinely interested and have done your research.

Step 7: Act Quickly After Meetings

If you’ve had any recent encounters with the recipient, send your email as soon as possible. This demonstrates that you’re proactive and keeps your interaction fresh in their mind.

Step 8: Be Persistent

Understand that persistence pays off. Stebbings sent 53 emails over a year to finally secure Benioff as a guest. If they don’t respond right away, it’s important to follow up thoughtfully.

Conclusion: Open New Doors

Ultimately, building connections and exploring opportunities is about putting yourself out there. Always seek options that lead to another opening. As Stebbings reflected, “Always take the option which has another door opening.”

Key Takeaways

  • Craft a compelling subject line that stands out.
  • Be direct and transparent about your intentions.
  • Use credibility to back up your request.
  • Personalize your message based on research.
  • Follow up quickly after initial meetings.
  • Embrace persistence for better results.
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TAGGED:29YearOldBenioffBreakthroughBusiness StrategyCashflowColdEmailsFounderInvestingMarcMoney Management.Passive IncomePaysPersistenceTurned
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