Episode Summary
Executive Summary: In this episode of Ask an Angel, Jason Calacanis and Zach Coelius discuss the evolution of angel investing post-COVID, focusing on the shift to Zoom meetings, red flags for investors and founders, and strategies for startup survival in a tough market. They emphasize the importance of relationship building, efficient time management, and avoiding over-optimization on valuation.
Main Topics: Post-COVID Investing via Zoom (Priority: 5/5): The shift to Zoom has increased efficiency and deal flow, allowing investors to see more pitches and make more objective decisions, though it may reduce relationship depth. Red Flags in Syndicate and Startup Deals (Priority: 5/5): Key red flags include high valuations without traction, lack of due diligence data, bridge rounds from well-known VCs, and investors who are impatient or micromanaging. Founder-Investor Relationship Dynamics (Priority: 4/5): Founders should vet investors through references and avoid those who are overly controlling or lack domain expertise. Investors should add value without creating unnecessary costs. Startup Survival Strategies in 2023 (Priority: 4/5): For startups with no path to profitability, options include pivoting, leveraging AI, cutting staff aggressively, or shutting down. Speed and decisive action are critical. Valuation Negotiation Philosophy (Priority: 3/5): Both hosts advocate for a take-it-or-leave-it approach to valuation, avoiding over-optimization to maintain good relationships and attract quality investors. Building Relationships with VCs Before Starting (Priority: 3/5): Natural interactions through shared activities or Twitter can build valuable relationships, but cold outreach for feedback is generally ineffective. Learning and Evolving as an Investor (Priority: 3/5): Coelius and Calacanis discuss how their early beliefs about reading founders have evolved, now emphasizing customer feedback and post-investment support.
Key Arguments: Zoom meetings are as effective as in-person for evaluating founders, but post-investment relationship building is crucial. Red flags in syndicate deals include high valuations without traction, missing financial data, and bridge rounds from top VCs. Founders should avoid investors who are impatient, micromanaging, or lack domain expertise; references are essential. Startups with no path to profitability should consider pivoting with AI, cutting staff deeply, or shutting down. Valuation should not be over-optimized; a fair price and good relationship are more important than a few extra million. Building relationships with VCs through shared activities or Twitter is more effective than cold outreach. Investors should focus on post-investment support, such as teaching founders accounting and planning, to improve outcomes.
Data Points: Time spent on new deals: 40-50% - Zach Coelius spends 40-50% of his time looking at new investment opportunities. Time spent on existing companies: 30-40% - Coelius spends 30-40% of his time helping portfolio companies. Revenue inflection point: $40,000 per month - Jason Calacanis identifies $40K monthly revenue as a key inflection point for startups. Series A revenue bogey: Over $1 million ARR with 3x+ growth - Coelius states that over $1 million ARR with 3x+ annual growth is needed for a Series A. Number of countries visited: 90+ - Zach Coelius has visited over 90 countries. Number of investments: 350 - Coelius has made approximately 350 investments. SOC 2 compliance time: 2-4 weeks with Vanta vs. 3-5 months without - Vanta customers achieve SOC 2 compliance in 2-4 weeks on average.
Pivotal Quotes: "If I do my job correctly, you don't need to call me because you don't need me because you're amazing. And I'm here to basically be helpful if you need an introduction or whatever when you're trying to raise money." — Zach Coelius: Coelius describes his philosophy as an investor: to stay out of the way and let founders execute. "My job is not to put costs on entrepreneurs. My job is to stay out of the way and let them go execute and perform. And my job is to pick people who don't need me." — Zach Coelius: Coelius emphasizes the importance of not burdening founders with unnecessary requests. "If you're optimizing for that extra $5 million, the most talented investor will say, okay, you know what? Maybe I'll invest in the next round. So let me know." — Jason Calacanis: Calacanis warns against over-optimizing on valuation, as it can deter quality investors.
Implications: The shift to remote investing is here to stay, requiring new strategies for relationship building. Founders must focus on performance over promise, and investors should prioritize adding value without micromanaging. The current market demands decisive action, with AI offering a potential lifeline for struggling startups.
From the Transcript
If I do my job correctly, you don't need to call me because you don't need me because you're amazing. And I'm here to basically be helpful if you need an introduction or whatever when you're trying to raise money. But generally, like that means I picked a good entrepreneur. And you shouldn't have me taking your time. So I should never ask you to do something that literally you think is a waste of time. And at the point that I ask you ever to do something that you think is a waste of time and it's a cost of the business, please tell me that. Be like, yes. Please tell me, hey, this is why I think this is a cost, not a positive ad. And then I can tell you why I think it's going to help the business or not. But my job is not to put costs on entrepreneurs. My job is to stay out of the way and let them go execute and perform. And my job is to pick people who don't need me. But the corporate people, oh my gosh, they just like live in this kabuki. There's a time for them. You know, if you get to series B or series C. No, there's never time to be a bad thing. Okay, well, there might be a time for.
Please tell me, hey, this is why I think this is a cost, not a positive ad. And then I can tell you why I think it's going to help the business or not. But my job is not to put costs on entrepreneurs. My job is to stay out of the way and let them go execute and perform. And my job is to pick people who don't need me. But the corporate people, oh my gosh, they just like live in this kabuki. There's a time for them. You know, if you get to series B or series C. No, there's never time to be a bad thing. Okay, well, there might be a time for. Somebody with, not the busybody ones, but somebody with deep domain expertise in finance. Sure. And you're thinking about doing a venture debt, and you don't have a CFO, and this person's an investor, and they got a lot of CFO experience, and you can put them on a mission to get four venture debt quotes. And you can use their mutant strength to not derail the management team, but to do work for the management team. And so that goes to how do you manage your investors? And so, you know, that's a really great thing to do: to tell people, like, hey, yeah.
How much money do you need to make it to the next level? And how much dilution do you want? So, okay, you need $3 million. Okay, you want to dilute no more than 20%. Okay, so you got a $15 million valuation, a $20 million valuation, it's somewhere in that range. And then you just test it with the market. And if you're happy with that valuation and you think it's reasonable, well, then both sides of the table can feel like they, you know, did a reasonable transaction and you can get back to work. If you're optimizing for that extra $5 million, the most talented investor. Will say, okay, you know what? Maybe I'll invest in the next round. So let me know. And then you get some sucker at the table who's trying to, and we talked about it before, maybe you're getting, you know, the finance guy or the, you know, send you on a wild goose chase mission gal who, you know, you don't want as investors. Now you just added somebody to the cap table because you're optimizing for valuation. It's a red fight for me. Like, in fact, the point that the entrepreneur is more focused on the value.
About This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.