One of the reasons I joined the current startup I’m at was to learn from a successful CEO/ founding team – to be mentored. So far, I’ve appreciated every moment.
It’s fascinating to me how he thinks. He’s highly successful with prior startups; so, to say his mindset is different from mine would be an understatement. In fact, we’ve approached many things from completely different perspectives.
Some observations and disparities in viewpoints:
  • Him: time and money (big). Me: test and money (small). Oftentimes, he thinks in time first, money second. He recognizes time is a resource we don’t get back. Meanwhile, time is also money. Recently, we debated about testing messaging. As I thought about testing variants for efficacy that may take time, he thought about burn rate. Specifically, how much time and money will have been spent for an effective test? He would rather test quickly and burn through a list, for example, and then get another list later, not go through 4 weeks of burn before finding something that works.
  • Him: Get results now, and get efficiency later. Me: Get results soon, and get efficiency later. To the point above, my CEO is acutely aware that we may have to freestyle a bit now which may be inefficient. However, he’s cognizant of what he needs now to show success. If we find success now, we can build out the right strategy to be more efficient and scale.
  • Him: top-down numbers. Me: Bottom-up numbers/ approach. Having boot-strapped my startups in the past, I think “organic”, bottom-up like acquisition. I think about acquiring a handful of customers through highly tailored approaches. I think about piecing together the grander message for marketing. My CEO thinks about conversions. He thinks about the math of filling the pipe with XX number of cold leads converting to YY leads converting to ZZ opportunities converting to AA customers. He thinks about what he can do now, how much more resources to commit to yield customers at the bottom. Then, refine the approach for scale.
  • Him: Get on the plane. Me: I’ll try to get them on the phone. That is, we need to learn as much as possible as fast as possible and keep everyone happy. From bootstrapping, I’m reticent to spend $100 on a customer (even if that fits in fine for our cost of acquisition). Again, I’m thinking about money, but from a “small pockets” perspective. For my CEO, I can spend what’s needed now (including hopping on a plane) to meet with prospects or working with an early customer to ensure we get the most out of our customers (beyond revenue). 
  • Him: Everyone pays. Me: Friends and family five-finger discount (free). Friends or not, if they find value, they’ll pay. I was always under the impression of giving a handful of friendlies free use of the product in exchange of learning. For my CEO, he wants to test if even his connections value our service enough to pay for it. That’s pretty important. Getting things free is great, and using it can be great. But that doesn’t tell you if you’ve created a product of VALUE.
  • Him: Your time is valuable. Me: I can discount my time. Same as the first couple points and the “finding value” bullet preceding, my CEO ensures contractors and the like get paid. When I was starting out, I offered to work for free as a trial to see if this relationship would be worthwhile. He was adamant on paying. It sets expectations. Free can discount effort. Don’t discount your value.

It’s been a fun ride, and I will continue learning from him. I haven’t set up explicit “mentoring” or “coaching” sessions. Instead, I’ve just taken so many mental notes on his approach to… everything. It’s fascinating, and I know this experience will pay off in the long-run. Heck, they’re paying off today.

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