Sep 8, 2017 · 32m · 20vc
20VC: How To Run The Perfect Fundraising Process, Why Time Kills All Deals & Why You Have To Get VCs Out Of The Board Room with Wayne Chang, Serial Entrepreneur & Angel Investor
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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 episode of The 20 Minute VC, serial entrepreneur and angel investor Wayne Chang joins Harry Stebbings to unpack key strategies for running an efficient VC fundraising process, scaling startup operations rapidly, and managing founder time. Drawing from his experience co-founding Crashlytics and investing in top tech unicorns, Wayne provides actionable advice on pitch dynamics, product design, hiring, and investor relations.
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 23.6% of the talking time here. How this is scored →
Harry as informed peer 3.5 Guest teaching 4.8 Guest disagreement 1.8 Harry pushing back 3.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:42 Wayne rejecting dilution premise
Wayne bluntly dismisses Harry's question about founder dilution, replying 'No, it doesn't mean that at all, actually' before detailing why capital efficiency shouldn't come at the cost of speed.
Hardest push from Harry ▶ 16:55 Harry questioning VC boardroom stereotypeHarry actively challenges Wayne's thesis that VCs force power dynamics in boardrooms, asking whether that stereotype of venture capital isn't already dying out.
Biggest teaching moment ▶ 7:19 Delta of Wow explanationAfter Harry confesses total ignorance about the 'Delta of Wow', Wayne delivers a clear lesson on comparing baseline user expectations against delight moments in product design.
Harry holds his own ▶ 14:00 Harry citing Mike Dauber on time killing companiesHarry demonstrates industry domain knowledge by bringing up a quote from Amplify VC's Mike Dauber to test and validate Wayne's perspective on startup velocity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Why Time Kills Startups & Early Recruiter Hiring | 3 | 5 | 1 | 4 | Harry challenges Wayne's recommendation of hiring an early recruiter by asking if it dehumanizes the hiring process and harms culture. Wayne politely reframes the premise, explaining that founders must reallocate their freed-up bandwidth specifically toward team bonding and retreats. | |
| Recruiting Persona & The 'Delta of Wow' Concept | 2 | 6 | 1 | 1 | Harry explicitly admits he has no idea what Wayne's 'Delta of Wow' framework means. Wayne takes full control to explain the concept using examples of government forms versus streamlined software installation at Crashlytics. | |
| The Triangle of Focus & Capital Allocation Strategy | 6 | 5 | 3 | 6 | Harry pushes back on Wayne's capital allocation advice, asking if over-investing in speed leads to severe founder dilution, and later quotes investor Mike Dauber on time killing startups. Wayne forcefully rejects the dilution premise, explaining that raising more capital to buy speed creates exponentially greater value. | |
| Fundraising Strategy: Escaping the Boardroom Dynamic | 5 | 4 | 3 | 6 | Harry challenges Wayne's tactical advice about avoiding VC boardrooms, questioning whether the arrogant boardroom VC stereotype is an era that is dying. Wayne disagrees, pointing out that VC ego remains deeply ingrained even if masked visually. | |
| Creating Fundraising Urgency, Handling FOMO & Networking | 3 | 5 | 2 | 3 | Harry asks probing questions about generating fundraising FOMO and navigating meetings with associates versus partners. Wayne breaks down the psychological dynamics of VC decision-making and advises against wasting time with low-level associates. | |
| Quick Fire Round: Insights, Mentorship & Recent Investments | 2 | 4 | 1 | 1 | Harry runs through standard quickfire questions covering book recommendations, personal philosophy, and recent angel deals. Wayne offers thoughtful reflection on his career and life stage without friction. |
Statements from this episode (12)
Wayne Chang: Time is the primary enemy of founders and startups
“My favorite thing I believe in is the enemy Of founders and startups is time. And so what does that mean? That means every day that goes by, you're becoming old news. Every day that goes by, your burn rate just goes up. No matter what happens, if you accomplis…”
Founders without recruiters spend up to 60% of their time hiring
“With recruiters, what I hear a lot with other founders is that they would spend 40 to 60% of their time just trying to recruit the team, trying to look through the resumes, go on Craigslist, things like that.”
Hiring an early in-house recruiter accelerated Crashlytics' maturity by years
“By the time that we were four months old, we had the startup DNA profile of a startup that's about two years old.”
Wayne Chang defines the 'delta of wow' in product design
“So you're able to go ahead and create an experience that is so outside the baseline norm. The difference between that experience and what the baseline is, is the delta of wow.”
Founders should prioritize speed and quality over cost when building
“What I believe my big bias is the two qualities you pick should be speed and quality, which means what you're giving up is the cost of it, which means it might be more expensive to produce higher quality things faster.”
Raising under $150,000 is one of the biggest mistakes founders make
“So one of the biggest mistakes I hear is entrepreneurs raising so little capital. They're saying, I just need 50,000 dollars to do this, or I'm just going to raise You know, 75, 150,000 dollars, which gives very little room for error or experimentation and giv…”
Founders who stretch a $1M seed round over six years are weak
“What would be the worst for me is to hear, you know, six years from now, same entrepreneur comes back. Hey, Wayne, thanks for the million dollar check. I was able to make it last for six years. That to me is the worst type of entrepreneur because they, they're…”
VC power dynamics and egos will never disappear despite market shifts
“I think visually it might be dying, but I think ego so much ingrained as part of human nature that I think that would never go away. It might be mass. I still know a lot of VCs that have mega power ego trips.”
Founders should never tell VCs which other investors they are meeting
“You never reveal who you're talking to the others, because VCs will always try to back channel each other. So you says entrepreneur raising, I believe you should never reveal while you're fundraising, who else you're fundraising from. That's only to your detri…”
Founders must force VCs to pitch their capital to the startup
“You're not selling your idea to them. You need to get them to sell their dollars to you. VCs are in the business of trying to get their capital and their money accepted by great entrepreneurs.”
Giving VCs or partners more time lowers the likelihood of deal completion
“The more time that VC has, the more A time that a potential vendor or partner has, the worse off you are, the less likelihood of a deal completion.”
Taking pitch meetings with outbound VC associates is a waste of time
“If it's an associate reaching out saying they want to talk and learn more about it, when I hear that, what I'm hearing is they're just trying to pump as much information out of you and then put into a database somewhere and send it to the partners. And those t…”