Sep 13, 2019 · 31m · 20vc
20VC: Clearbit Founder Alex MacCaw on How To Successfully Negotiate with Investors, What Value-Add Do VCs Really Bring & Why You Should Only Have Operators on Your Board
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In this episode of The 20 Minute VC, host Harry Stebbings speaks with Clearbit founder and CEO Alex MacCaw about the operational pillars of scaling a startup, cultivating conscious leadership, and taking a contrarian approach to venture capital and board governance.
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 40.9% of the talking time here. How this is scored →
Harry as informed peer 2.8 Guest teaching 2.9 Guest disagreement 1.7 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:36 Alex reframes VCs as salespeople selling financial instruments
Alex delivers his most contrarian critique of venture capital, stripping away prestige by characterizing VCs as professional salespeople and insisting leverage only comes from profitability.
Hardest push from Harry ▶ 15:43 Harry challenges the affordability of founder health perksHarry pushes back directly against Alex's recommendation of full-time chefs and gym stipends, questioning how seed-stage founders with limited cash can realistically justify those expenses.
Biggest teaching moment ▶ 19:18 Alex details the Above/Below the Line conscious leadership modelAlex takes time to thoroughly educate Harry on the psychological dynamics of conscious leadership, explaining how leaders shift between open states of trust and defensive states of threat.
Harry holds his own ▶ 8:25 Harry brings up Patrick Collison's hiring methodologyHarry displays sharp domain knowledge by citing Patrick Collison's process of interviewing dozens of experts to benchmark what exceptional candidates look like before making a hire.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Initial Guest Greetings | 3 | 2 | 1 | 2 | Harry asks Alex about his founding path and brings up Mathilde at Front to probe whether early company mission statements are overstated compared to operational discipline. Alex agrees with Mathilde's emphasis on operations while clarifying his view of a company as a personal self-growth vehicle. | |
| Transitioning to the Company-Building Phase | 2 | 3 | 1 | 2 | Alex defines company building as building the machine that builds the machine and credits CEO coach Matt Mochary. Harry asks a direct question about how Alex managed this transition as a first-time founder without hindsight, which Alex answers by highlighting the importance of asking for help. | |
| Pillar 1: People and Upfront Hiring Excellence | 4 | 2 | 1 | 1 | Alex discusses hiring as the primary pillar of management. Harry demonstrates domain familiarity by referencing Patrick Collison's tactic of meeting multiple top performers in a role to benchmark excellence, leading Alex to share Clearbit's team sourcing sessions. | |
| Pillar 2: Autonomy and Delegated Goal Setting | 3 | 2 | 1 | 2 | After discussing autonomy and OKR setting, Alex advocates default transparency. Harry pushes on the risks of total transparency during fundraising by referencing Jeff Seibert's observations, prompting Alex to explain his biweekly updates approach. | |
| Pillar 4: Feedback Culture and Radical Candor | 2 | 3 | 1 | 2 | Alex emphasizes Radical Candor and direct feedback. Harry asks a personal question about overcoming people-pleasing tendencies, to which Alex explains his Enneagram 8 Challenger profile and why external validation isn't a driver for him. | |
| Pillar 5: Health and Work-Life Harmony | 3 | 3 | 2 | 4 | Alex presents work-life harmony and health stipends as critical. Harry pushes back on how early cash-strapped founders can afford chefs and gym stipends, and Alex counters that founders cannot afford not to invest in their health. | |
| Pillar 6: Management and Conscious Leadership | 3 | 4 | 1 | 2 | Alex admits Clearbit's onboarding needed work and introduces the Above/Below the Line conscious leadership model. Harry references Clark at InVision regarding journaling for self-awareness and asks probing questions about trust deterioration. | |
| Negotiating with VCs and Term Selection | 3 | 4 | 4 | 3 | Alex takes a contrarian stance on VCs, calling them salespeople selling financial instruments and dismissing firm prestige. Harry challenges whether premier VC brands actually help with executive recruiting, which Alex dismisses as vanity. | |
| The Value of VCs and Unbundling Venture Capital | 3 | 4 | 3 | 2 | Alex states he asks VCs for no operational help and prefers keeping investors off his board in favor of operators. Harry brings up Naval Ravikant's unbundling VC thesis and probes on the right stage to establish a formal board. | |
| Quick Fire Round, Culture Scaling, and Future Vision | 2 | 2 | 2 | 3 | In the quick fire round, Alex discusses his forthcoming management book centered on leading with love and vulnerability. Harry directly questions whether leading with love can scale to a 1,000-person company, and Alex candidly concedes they will see. |
Statements from this episode (19)
MacCaw Founded Clearbit as a Vehicle for Personal Self-Actualization
“I actually started this company as a tool to self actualize.”
MacCaw: Interviews Fail; References Are the Only Reliable Evaluation Method
“But I do believe that frankly, interviews just don't cut it. You know, the only real way we found of evaluating candidates is through references and back channels.”
MacCaw: Operations and Management Determine Post-PMF Startup Success
“Operations and management are the unglamorous side of company building, sure, but after product-market They are the difference between success and failure.”
Executive Coach Matt Mochary Coached Clearbit for Free in Its Early Days
“Matt Mashari helped us in the early days, and he didn't charge us a thing.”
MacCaw: Hiring the Right People Upfront Is 80% of Management
“I think what is less understood is that 80% of the work of management is actually done up front by hiring the right people.”
MacCaw: Mandatory Employee Sourcing Sessions Are the Best Way to Scale Hiring
“So the secret is sourcing sessions. Sit down with your engineers or whoever is relevant for the role and then use tools. There's tools like teamable, or you can just go through the LinkedIn and use LinkedIn recruiter. You literally just got to sit them down be…”
MacCaw: Clearbit Keeps the Exact Same OKRs for the Entire Year
“What we do is the leadership team gets together and we'll figure out the company OKRs at the start of the year, and we actually have the same OKRs the whole year. And that includes the revenue number, but it also includes a number of other things that we're wo…”
MacCaw: Clearbit Maintains Default Transparency Except for Compensation and Performance
“To be clear, we are transparent in all areas by default, aside from compensation and performance.”
MacCaw: Minute-by-Minute Fundraising Updates Distract Startup Teams
“So you should be transparent, but giving people the minute by minute play by play updates to the funding round is just going to distract them.”
MacCaw: Clearbit Perks Include Full-Time Chefs and Therapy for All Employees
“We actually have two full-time chefs, because people just pick the default. If there's shitty food in front of them, they'll pick it. We offer gym stipends. We offer therapy for everyone. We offer the best health insurance. We have on track vacation. You can w…”
MacCaw: Founders Should Put Personal Trainers and Therapists on the Company Card
“As soon as you raise that first round, or you get to profitability, then put a personal trainer on the company card, put an exec coach on the company card, put a therapist on the company card. These are absolutely legitimate expenses, and you should be spendin…”
MacCaw: Venture Capitalists Are Just Salespeople Selling Financial Products
“So the first thing to realize that VCs are professional salespeople. That's all they are. They're salespeople that sell financial instruments.”
MacCaw: Profitability Is the Only True Leverage Founders Have With VCs
“If you can't walk away, you have no leverage. So get profitable. It's the only way you can walk away.”
MacCaw: Founders Should Ignore VC Brand Prestige and Prioritize Clean Terms
“The second piece of advice I have for negotiating with VCs is to stop caring about external validation. So stop caring about the glamour, about the big name VC, None of it matters in my opinion. You're simply trying to sell a piece of your company for the clea…”
MacCaw: Clearbit Expects Minimal Operational Help From Its VC Investors
“I tell our VCs that I actually don't want much help from them. If I want a recruiter, I'll pay for a recruiter, and there'll be a better recruiter than that VC because they're full-time.”
MacCaw: Clearbit Received Zero Recruiting Candidates From Its VC Investors
“Honestly, we had no candidates through our existing investors or through other investors”
MacCaw: Clearbit Will Add Operators, Not Investors, to Its Board
“So we will set up a board, and I'm planning on doing it next year, but we're going to add more operators to it rather than have any investors on it.”
MacCaw: Startups Should Delay Establishing a Formal Board Until Series B
“Definitely not for the seed. I would just raise the seed on all safes. For the A, try not to add to the board, and then maybe the B. Often you just don't have a choice. A lot of investors will require being on the board. There's kind of a luxury having the cho…”