Lenny’s Newsletter · Free post · Startups & founders · Communication & influence

A playbook for fundraising

Practical advice for navigating the fundraising process by Marc McCabe

Lenny RachitskySep 1, 202021 min♥ 92
SourceLenny’s Newsletter
KindFree post
PublishedSep 1, 2020
Readers♥ 92
Originallennysnewsletter.com ↗
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Marc McCabe, an experienced angel investor who has helped dozens of startups raise money from pre-seed to Series C, argues that fundraising is best treated as a structured, trust-building process rather than a scramble when cash runs low. He targets founders of tech companies preparing a Series A and walks through four stages: preparation, outreach, running the process, and partner meetings with closing. The guide emphasizes telling a compelling story, hardening the pitch with test audiences, keeping all target funds on a similar timeline to create competition, and handling term sheets and closing carefully. It is most useful as a practical playbook for founders planning their next round, though it reflects US-centric, pre-pandemic-era assumptions in places.

01Key takeaways

  • Raise from strength, ideally with eight months of runway, rather than when cash is almost gone.
  • Test your pitch on four to six people before pitching real investors, then refine the story.
  • Build a list of 50 to 60 funds and secure warm introductions, ideally from portfolio founders.
  • Schedule first meetings within a two to three week window so no fund gets ahead of the others.
  • Create competition among funds so you are not forced to accept the first term sheet.
  • Anchor valuation discussions toward the top of your range and focus on capital needs and key terms.

02Key sections

Preparation
Founders should raise when they have proven a credible value hypothesis and growth, not when they are out of money. Materials include a blurb, teaser and full decks, a forecast, and optionally a metrics deck, prepared over several weeks.
Hardening the pitch
Before real meetings, the pitch is refined to about 70 percent completeness and tested with four to six trusted people. This builds confidence and can yield useful feedback and warm introductions.
Outreach
Build a list of 50 to 60 funds that can write a lead check, identify the right partners, and secure warm introductions, ideally from founders in the fund's portfolio. Keep at least eight months of runway when starting.
Navigating the process
Schedule first meetings within a two to three week window so funds progress on similar timelines, and track each fund's next steps. Expect most funds to pass, so several interested funds at diligence stage is considered a success.
Partner meetings and closing
Once a partner champions the deal, the founder and partner become allies. Use term sheets carefully, have legal counsel review terms, and expect several more weeks of legal work before money arrives.

03From the post

“Hello, I’m Lenny and welcome to afree monthly editionof my weekly newsletter. Each week I humbly tackle reader questions about product, growth, working with humans, and anything else that’s stressing you out at the office. If you’re not a paid subscriber, here’s what you missed this month: 1. How to increase retention 2. Flywheels, flywheels, flywheels 3. Navigating your early career Q: I raised a small seed round, and I’m now thinking about raising our next round. Do you have any advice for navigating the process? Whenever I need fundraising advice, there’s one person I immediately go to: Marc McCabe. Marc is a friend, a former colleague, and a prolific angel investor. He has personally helped dozens of startups raise money (even doing this full-time for a number of years). When I got this question, I went straight to Marc and asked him to do a guest post. Not only did he agree, he ended up putting together the most comprehensive fundraising guide I’ve ever seen, which you’ll find below. Thank you Marc 🙏 If you have any further questions,…”

“Fundraising is, in the parlance of our times, a total head fuck.”Marc McCabe · Lenny’s Newsletter
“Ultimately, fundraising is an exercise in building trust.”Marc McCabe · Lenny’s Newsletter
“Having five VC partners still interested in investing after the diligence phase is a success.”Marc McCabe · Lenny’s Newsletter

04Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.