I met Max when he was in undergrad and visiting SF as part of Princeton’s annual TigerTrek. Then years later we reconnected at Google (where he was a Product Manager) for a GV BBQ. It was so much fun catching up that soon after as he started Warmly I was fortunately given the opportunity to angel invest. Since that time the company has evolved and grown, but even more so, Max has done the same! And I’ve gotten to see him figure out what kind of leader he wants to be. One who is currently building his company in public [ie sharing a bunch of data, progress, and even setbacks, that a startup founder might normally not disclose]. Recently I asked him to join me for Five Questions where we could talk a little bit about his journey.

Hunter Walk: Your startup Warmly recently turned four years old. If 2024 Max could magically whisper one learning, or piece of advice, into the ear of 2019 Max, what would it be?

Max Greenwald: I would whisper: You will pivot, probably multiple times. Don’t stress over making anything perfect, or answering every email. Focus maniacally on tossing a ton of spaghetti at the wall and if there is any inkling of PMF you feel it. Keep searching until you feel it. Looking back I see that 99% of the emails I sent were useless.

HW: Warmly has done some co-marketing with Zoom and launched as one of their earliest ‘Zoom Apps.’ I’m generally skeptical of early stage startups trying to work closely with large platforms, but I understand why the opportunities are tough to pass up. Founders who are considering these sorts of ‘partnerships,’ are there red flags they should proactively look for in order to not waste time?

MG: Absolutely: it has mostly been very, very difficult working with a larger platform, especially a nascent one. App stores need 2+ years to mature before they’re any good. We should not have pinned so much hope to them early on to carry us to victory. Now after 2 years we are at a point where it’s “starting to work” but we spent months chained to the whim of their product roadmap. As an example: while we were waiting for Zoom for 2 years to get their shit together so we could unlock $600k ARR, we built an off-Zoom pivot (now our main business) that went 0 to $1M in ARR in 13 months.

HW: Your initial wedge was/is a virtual nametags products, but you’ve seen even faster revenue growth with the second product, a warm leads sales tool. I don’t consider this a true ‘pivot’ because they’re all aimed at the same mission, but it’s definitely expansion adjacently vs focus on a single SKU. With multiple cofounders was there consensus internally around the new work, or did people have various opinions about where/how to grow?

MG: I really like your pivot article. There’s also a silly stigma around pivoting. Here are Warmly’s 7 “pivots” over 4 years. In the latest iteration, my cofounders Alan/Carina staged a coup and told me that they didn’t feel like we had PMF and that our strategy to wait and see if our enterprise deals came through for our Nametags product was going to kill us. 

I think I was holding on too tight and they were right.

I had to dig deep to think if I had the energy for yet another pivot and came back saying yep lets do it. However we hedged our bet for 3-4 months and did both. This was risky but paid off since now our Nametags business is profitable and growing and our new one is the “big business” and we will get it to profitable

HW: When you’re hiring are there any particular attributes or experiences you look for which you value perhaps more than the average founder, or which you think are great signals the team member understands what they’re getting into with startup life?

MG:

Never hire from big companies: We both come from Google so don’t shoot me for saying that over time I’ve learned never to hire from Google or big tech in general for early stage roles. All but 1 of the big company people I hired who said they were so excited to try their first startup role were fired or left within 6 months.
Slope > Y-intercept: Slightly math-y but we over index on whoever we think can learn the fastest. If you’re slope (your rate of learning) is higher than someone who has a lot of experience (a high y-intercept), then within a year or so the fast learner will outpace the more senior person

HW: When you talk with other CEOs, what’s the vibe heading into Summer 2024? 

MG: Vibes are

• Series B+ markets are frozen. Series A’s need to get to profitable or die
• Really trying to find and look for investing benchmarks and salary benchmarks for the new more lean age we are in

Thanks Max!