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Today I want to share some lessons from a tweet shared with me by a subscriber. The tweet features a video from Doola CEo Arjun Mahadevan discussing lessons he learned while fundraising. The link with video is below, but I’ll summarize his six key tips as well:
I’ve raised $13M for doola.
But I made a *ton* of mistakes along the way.
In this video, I break down the biggest lessons I learned — so you can avoid the same pitfalls and raise with confidence.
Whether you’re raising your first round or trying to level up, this is the
— Arjun Mahadevan (Mr. LLC 🇺🇸) (@ArjunMahadevan)
1:00 PM • May 5, 2025
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Arjun’s tips:
Rule of Sixty - It takes 60 conversations to get a cheque. I’ve shared this many times, although my experience puts the number closer to 25 than 60. The key, however, is that 60 isn’t the number of emails, contacts, or outreach; it’s the number of conversations you have. The reality is that if you have 180 warm intros, you might get 90 conversations. If you send 600 cold emails, you might get 60 conversations. So when founders complain they are struggling to raise, the reality is that for 99%, they don’t understand these numbers and haven’t even put in enough reps to justify complaining that they can’t get it done.
Raise in Tranches - Instead of raising all at once, Arjun recommends raising in tranches. This is a strategy I haven’t recommended or used with clients, but I do think I will be using more moving forward. The idea is that instead of raising $1M at $10M, if that is your goal, you can raise in tranches. So start with $100k at a $7M valuation, then tell investors once that is commited you will raise the next $100M at a $8M valuation, and so forth. This can work well as you often raise at a higher average valuation than the $10M, and you also create urgency for investors and get them to bite immediately.
Investors CRM - This is 100% something you need to do. I have the same investor CRM that is available to all the founders I work with, and it is a lifesaver. You need to track where you are with investors at all times.
55/38/7 rule - This is the idea that only 7% of what investors receive from you is from the spoken words. The other 93% is from tone and body language. So you need to nail the nonverbals. This goes back to the social status I always talk about and how that should be the core focus of your pitch.
Fill the Cup - People invest in you if they know you. So you need to chat with investors and build relationships even before you are raising. This is something I’ve also pushed with monthly investor updates, which I believe should be a standard for all companies.
Believe the No, Ignore the Why - When you get a no, you need to understand that this isn’t a fit, but that doesn’t mean the reason investors give is correct. Generally, they are wrong or specific to that investor, as the founder, you need to know your company better than they do.
Should I do more issues like this with insights from founders who have raised? |
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