Feb 5, 2022 · 42m · news
Mac the VC on the Journey from Homeless To Becoming A VC | Full Interview with Harry Stebbings · 20VC with Harry Stebbings
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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 20VC, Mac Conwell shares his unconventional journey from startup failure to launching Rare Breed. He outlines his rule-breaking approaches to fundraising on Twitter, his focus on overlooked geographies, and his mission to democratize venture capital through empathy and structural innovation.
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 17.4% of the talking time here. How this is scored →
Harry as informed peer 3.5 Guest teaching 3.5 Guest disagreement 2.5 Harry pushing back 1.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:12 Rejection of top-tier fund co-investing
Mac forcefully attacks conventional VC advice that emerging managers need top-tier fund co-investors, explicitly stating 'I don't give a fuck about a hot deal' and calling the standard strategy mediocre.
Hardest push from Harry ▶ 14:15 Harry defending hot deals as LP signalingHarry directly challenges Mac's dismissal of hot deals by explaining that getting into rounds with Sequoia or First Round is essential for signaling to LPs during future fundraises.
Biggest teaching moment ▶ 30:00 Mathematical flaws of rolling fundsMac educates the host on the specific mechanics of rolling funds, explaining how quarterly siloed allocations disadvantage early smaller LPs who miss out on fund-returning deals made in subsequent quarters.
Harry holds his own ▶ 14:15 Harry demonstrating LP fundraising mechanicsHarry shows his deep understanding of institutional VC dynamics by clearly explaining why VCs chase brand-name follow-on investors to construct a narrative for LP pitch decks.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| From Startup Failure to Venture Breakthrough | 1 | 2 | 1 | 1 | Harry asks open-ended questions about Mac's unconventional entry into venture capital and how he handled the failure of his second startup. Mac shares a personal account of his depression following failure and his eventual realization that personal support was unconditional. The dynamic is empathetic and exploratory with no friction. | |
| Fostering Human Connection and Vulnerability with Founders | 2 | 3 | 1 | 1 | Harry prompts Mac to explain his founder-first approach and how he leveraged Twitter to raise his fund. Mac details how social justice movements and Twitter DMs enabled him to set up over 1100 meetings to soft-circle his first fund. Harry listens and asks follow-ups on response rates in a collaborative spirit. | |
| Breaking Traditional VC Rules for Fund Structure | 3 | 4 | 4 | 2 | Mac aggressively criticizes conventional venture capital fundraising rules, detailing how he ran rolling closes, waived GP commits, and structured custom capital call options. Harry probes on practical realities like legal expenses and GP commit requirements, allowing Mac to explain his pro-bono legal arrangement. | |
| The Reality of Hot Deals, LP Diversity, and Tokenism | 5 | 5 | 6 | 4 | Mac rejects the premise that emerging managers must co-invest with top-tier funds to access good deals, dismissing 'hot deals' as meaningless compared to capital returns. Harry offers an informed counterpoint, explaining that co-investing with Sequoia is used as a signaling mechanism for LP fundraising. Mac holds his ground and further critiques lip service around diversity at institutional LP levels. | |
| Rare Breed's Portfolio Design and Regional Investing Strategy | 5 | 3 | 1 | 2 | Harry asks sharp, technical portfolio construction questions regarding check sizes, target company counts, and reserve strategies. Mac outlines his approach to maximizing pre-seed multiples and regional investing across non-traditional tech hubs in an agreeable, detail-focused exchange. | |
| Overcoming Imposter Syndrome and the Power of Community | 3 | 3 | 1 | 1 | Harry openly shares his own technical shortcomings with spreadsheets, creating a peer level of mutual vulnerability around imposter syndrome. Mac shares how Stanford's VC program helped validate his skills and how early write-offs kept him grounded despite rapid social media growth. | |
| The Disadvantages of Rolling Funds and a Modern Alternative | 5 | 5 | 4 | 2 | Mac breaks down the hidden structural flaws of rolling funds for early LPs and explains how he combined a 506(c) structure with Carta and Anduin to replicate rolling fund benefits without LP disadvantages. Harry reinforces Mac's point by citing his own knowledge of LP behavior regarding capital commitments. | |
| Advice for Emerging Managers and a Vision for Baltimore | 4 | 3 | 2 | 1 | Mac offers advice for emerging managers and lays out his 10-year vision to build a top-tier multi-stage VC firm in Baltimore. Harry probes on whether follow-on investors truly look past regional biases, and both agree that top-line growth metrics like 40% MoM overcome any geographic prejudice. |
Statements from this episode (25)
Mac Conwell broke into venture capital without a degree or finance background
“I'm like, ok, I don't have a college degree, I don't have a finance background, but I know startups, and I know a lot of people in Baltimore,”
Harry Stebbings was rejected by many venture capital firms early on
“I got rejected by many venture firms, which not many people know, but we are going to have an open conversation today.”
Mac Conwell returned remaining capital to investors after his second startup failed
“I basically Got burnt out. Told my investors, hey, thanks, but no thanks. Here's what little money we have left. You can all have it back.”
Mac Conwell held over 1,100 meetings to soft-circle $2 million
“Between June, the middle of June, 2020 to September, 20, 20, I had over 1100 meetings, which allowed me to soft circle my first two million and kind of gave me the confidence to quit my job and Really go do this thing.”
Mac Conwell achieved a 75% response rate cold-DMing VCs on Twitter
“It was like, 70, 75%, because at the end of the day, in the world of venture, we're all happy to meet each other, because everybody's looking for deal flow, right?”
Mac Conwell offered RareBreed LPs flexible multi-year capital call options
“No, I gave my LPs three options. You can do a hundred percent upfront, 50% each year over two years or 33%. Over each year, over three years, with the minimum being 10 K per year.”
Mac Conwell raised RareBreed Ventures with zero GP capital commitment
“So I have no GP commit. I didn't have the money for it.”
Mac Conwell was not an accredited investor when starting RareBreed Ventures
“I wasn't even an accredited investor when I started raising my fund, right?”
Mac Conwell received over a year of free legal work for RareBreed
“He's never charged me. He's been my lawyer for over a year. He's never sent me a bill.”
Yale Endowment was the first institutional LP to address post-2020 diversity
“Name one pension fund that said anything. The first people to say something was really Yale, like five, six months later. And even then nobody else said anything because they don't have to say anything because nobody knows who they are.”
Mac Conwell states 77% of RareBreed portfolio founders are underrepresented
“77% of my portfolio are underrepresented founders”
Mac Conwell funded five startups sourced by diverse associates whose firms passed
“In one case, I had one of these associates. They've sourced three deals for me. I've had another one source too. And I know they're good deals. Follow a funding show. They're good deals. So why don't their firms appreciate the deals they're bringing up?”
RareBreed Ventures plans to back 40 to 45 companies in Fund One
“We're going to do somewhere between like 40 to 45 companies.”
RareBreed Ventures plans follow-on checks for only 6 to 10 portfolio companies
“We're going to do somewhere in the neighborhood of like six to 10 follow on.”
RareBreed Ventures invested $100,000 in MainStreet's $60 million funding round
“We got to be a small check in the second round of Main Street. For those who don't know, Main Street's second round was a sixty million dollar round. I got to put a hundred K check on that round.”
Mac Conwell admits his first three pre-seed investments failed completely
“When I was working for the investment arm for the state of Maryland, you know, We started this pre-seed fund for underrepresented founders, and they got all this hype, and everybody's excited, like, oh, you're doing these amazing things. The first three compan…”
Mac Conwell grew his Twitter following from 2,500 to 50,000 in months
“Last June I had 2500 followers, right? Like 10 years. 2500 people. I went from 2500, I think I just crossed 50,000, like yesterday.”
Mac Conwell argues rolling funds reflect a lack of VC innovation
“I think rolling funds are another sign of the lack of innovation in our industry, right?”
Mac Conwell explains how rolling funds disadvantage LPs who skip quarters
“LPs have to continuously buy in the quarters to make sure they get allocation to the companies you invest in. So if you're not an LP in the specific quarter and that's the quarter I make my best investment in, but you're an LP in the quarter before the quarter…”
Multiple LPs invested in RareBreed Ventures without ever speaking to Mac Conwell
“I've had quite a few LPs signed up to be LPs without ever talking to me.”
RareBreed Ventures executes rolling fund closes every three weeks
“I'm gonna do a roll and close every three weeks, so as our LPs come in, I just want you to close on them.”
Mac Conwell: VCs ignore location bias if growth reaches 40% month-over-month
“They care about money. So if you have strong enough metrics, they find a way to get over themselves, no matter where you're from. And that's all. And that's why I tell my founders, like, Hey, there may be biases against you. People may say, if you don't live c…”
Mac Conwell warns that starting a VC firm is a 20-year commitment
“And once you decide you're going to start a firm, you're basically making a 20 year commitment, right? Fund one's 10 years. Two, three years later, you're going to raise fund two. That's another 10 years. Two to three years after that, you'll raise fund three.…”