Dec 21, 2022 · 26m · 20vc
20VC Special: How To Fundraise Like a Pro: How to Size and Price a Round, How to Create FOMO and Urgency in a Fundraise, How to Structure Angel Allocations, The 7 Deadly Sins of Fundraising Decks, The 3 Signs a Potential Investor is Bad News
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this masterclass episode of 20 Growth, Harry Stebbings delivers a step-by-step playbook for startup fundraising, covering investor pipeline creation, pitch deck design, round sizing, term sheet urgency, and angel cap table strategy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 99.5% of the talking time here. How this is scored →
Harry as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Harry pushing back 0.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:58 Forceful criticism of bad VC terms
In this solo monologue segment, Harry forcefully denounces predatory VC tactics like charging founders to pitch or insisting on investment tranches.
Hardest push from Harry ▶ 11:35 Refuting absurd market sizing slidesHarry pushes back against widespread founder mistakes by mocking unrealistic trillion-dollar total addressable market slides for niche businesses.
Biggest teaching moment ▶ 9:36 Educational masterclass on deck constraintsHarry directly educates startup founders on strict deck rules, explaining why decks must remain under ten slides with concise framing.
Harry holds his own ▶ 13:22 Demonstrating venture math expertiseHarry demonstrates deep institutional venture expertise by explaining how lead VC ownership targets dictate minimum round sizing and cap structures.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Building a Tiered Investor Pipeline | 0 | 0 | 0 | 0 | Harry Stebbings delivers a solo monologue detailing how to build a tiered investor pipeline without guest involvement. Host-side scores are zeroed as required for monologue segments. | |
| Executing Pitch Meetings and Iterative Pitch Refinement | 0 | 0 | 0 | 0 | Harry explains pitch iteration and meeting strategy in a solo masterclass format. Because there is no guest interaction or host-guest dialogue, all four dynamic scores are 0. | |
| The 7 Deadly Sins of Pitch Decks | 0 | 0 | 0 | 0 | Harry lists common mistakes founders make in pitch decks during a monologue lecture. Without interactive dialogue, host and guest scores remain at 0. | |
| Sizing, Pricing, and Runway Planning for the Round | 0 | 0 | 0 | 0 | Harry presents guidelines for round sizing, pricing, and runway targets in a solo presentation. All scores are set to 0 due to the lack of dynamic host-guest interaction. | |
| Selecting Lead Investors, Creating Urgency, and Managing Term Sheets | 0 | 0 | 0 | 0 | Harry advises founders on evaluating lead investors and term sheet dynamics in a monologue format. Scores remain 0 given the solo lecture structure. | |
| Structuring Angel Allocations and Closing the Round | 0 | 0 | 0 | 0 | Harry concludes his solo episode by advising founders on angel cap table construction and post-close communication. Interactive scores are 0 for monologue content. |
Statements from this episode (21)
Wolt received 68 Series B rejections before 83North invested
“For his Series B, he got 68 rejections before Laurel Bowden at 83 North said yes.”
Stebbings: VC references from failed startups reveal their true character
“Place even more weight on their recommendation if the company has not been a success. It is easy to be a VC champion when the company is flying. You often see the true colors when a company is really struggling or fails.”
Stebbings: 150 of 200 daily pitch inbounds fail stage or sector criteria
“I get about 200 inbounds per day across different channels. About a 150 are clearly not a fit for me because of stage, sector, or geography”
Stebbings: Founders should pitch lower-priority VCs first to refine pitch
“They go to their priority names first. Do not do this. Your pitch both in delivery, style, and messaging will improve so much with each meeting. Start with a couple of investors where, respectfully, you would not be so sad if they said no.”
Stebbings: Limit initial pitch calls to two team members max
“If you're doing a Zoom call and it's a first meeting, do not have more than two people on the call from your team. It makes it tough to really get to the core of the discussion, and removes a lot of the relationship building with Too many people on a call too …”
Stebbings: VCs have a duty to review pitch decks before meeting founders
“I would have asked for a deck pre the meeting, and I as the VC should have gone through this beforehand. That's really my duty as a VC to have done the work beforehand, and so in the meeting we can really spend the time to double click or try and expand upon m…”
Stebbings: Advisor slides carry little weight with VCs
“Advisor slides just carry such little weight these days. They've been so overused. They're not worth having.”
Stebbings: Exit slides in pitch decks encourage short-term investment thinking
“Exit slides have no place in the slide deck. I do not see this so often now, but it really just attracts the wrong type of investor if they're looking for an exit on the day of their investment. It encourages short-term investment thinking.”
Stebbings includes a 'why not to invest' slide when pitching his funds
“Always I have when I'm presenting my funds in a slide, I have a slide at the end which says why you should not invest in me.”
Stebbings: Lead VCs require at least 8% ownership
“So VCs that lead, and you would want to lead, they need to own at least eight percent. Very, very minimum.”
Stebbings: VCs spend less time on checks under 1% of fund size
“For example, if the check size they are investing is less than one percent of their fund, It's not that meaningful. If it's less than .5%, it's really not that meaningful. Now this could be bad, as it means that they are unlikely to be able to provide you with…”
Stebbings: Startups should raise for 24 months of runway
“Rule of thumb, never raise less than 18 months. You also do not... You also do not need to raise more than 36 months. If we plan for a six-month fundraise, and the fact that execution 99% of the time always takes longer than you anticipate, I always choose 24 …”
Stebbings: Standard startup rounds assume 15% to 20% dilution
“The truth is, when you say the size of your fundraise, say two million, the basic assumption is that each round will dilute 15 to 20%, and so the average VC will think of a ten million post money valuation, Straight away, when you say a two million raise.”
Stebbings: Removing an investor is harder than getting divorced
“It's literally harder to remove an investor than it is to get divorced.”
Singerman: In-person meetings were necessary to invest during COVID
“Brian Singerman at Founders Fund said on the show recently about how he was unable to do his job in COVID as he could not meet founders in person”
Stebbings: 14 days is the optimal fundraising decision timeline
“14 days is perfect. This is enough time for any VC to do the work they need to do, but also if they cannot do it in that time, without a plausible excuse, it's unlikely they would have done the deal anyway”
Stebbings: Do not lose the ideal investor over valuation
“If the chosen partner is slightly lower, just take it. Do not lose the right partner because of a small percentage difference. In price or size of round.”
Stebbings: Early-stage founders should reject tranched investment structures
“If it's an early round, and the investor wants to invest in investment tranches, this is where they invest a little bit now, and then if you hit milestones, they'll give you more later. That is an investment tranche. Do not accept this either. This is complete…”
Stebbings: Treat angel cap table assembly like building a sports team
“When planning your angel allocations, I always advise founders to assemble their angel cap Table as they would a sports team. Each person has a specific position which they are specialized to and have a world-class skill in. So you have someone for marketing, …”
Stebbings: Give larger check allocations to fewer angels to maintain engagement
“A massive mistake I see often, is founders who try to cram down all their angels to their smallest allocation so they can fit in as many as possible. Do not do this. Give less people More allocation. It's really important that the check size that you give them…”
Stebbings: Immediately align with new lead VCs on milestones for next round
“In preparation for the next round, the most important thing is investors invest in lines and not dots, and so I would sit down with your new leads and align in that first meeting on five names that would be ideal leads for the next round, and then also clearly…”