Seven ‘Pivots’ Later, Warmly Finally Found Its Stride. CEO Max Greenwald Covers What He Wishes He Knew At The Beginning, and More…

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…