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.

I often hear how building a startup is like getting an MBA but on the job. Having an MBA and built a couple startups, I can say that it’s true… at least, partially. The downside of learning as you go is the otherwise lack of guidance and not knowing what you don’t know.
When I was at Body Boss, I had little experience in sales and marketing; however, I was the “Head of Business Development”. In a startup with three other partners with no experience in business development, I was the head, the foot, and the @$$.
I was always heads-down trying to figure everything out. I needed to learn a lot while tending to everything in front of me. This meant I didn’t dedicate time to self-development. Meanwhile, I was deep in the weeds without stepping back to see if I was oriented in the right direction.
Since Body Boss, I’ve taken steps to help cover the areas I don’t know while also accelerating learning in the areas that I care deeply about. (E.g. I’m no longer learning how to build iOS apps!)
Two ways I’m proactively seeking to deep learning:
  • Read books! I used to hate reading growing up – the books did not interest me. Meanwhile at Body Boss, I wore so many hats that I focused on short online articles so I could maintain breadth of learning. Now that I’m doubling down on sales and marketing (growth), I am seeking depth in my self-education by reading specialized books (reading The Challenger Sale now).
  • Seek mentors, coaches. I’m a big connector/ networker, so it’s curious why I didn’t reach out earlier for help and guidance. Perhaps I was too cocky to seek help before. Four years into this startup life, I’m wiser knowing there are plenty of people who know more than me and can help. I have mentors guiding me – talking entrepreneurship and other facets of life that influence my vision and goals. I’ve also actively sought out coaches – experts in specific areas who can guide me.

Startups and entrepreneurship have ignited a deeper hunger to learn. I’m definitely not a know-it-all. Instead, I’ve become a learn-it-all. Well, learn with specificity.

I recently had a couple interns work for me at SalesWise. They were great resources to help in marketing, sales, prospecting, support, etc.
However, the interns were straight out of high school (or still in). They did not have much experience in any particular area. It was a challenge, at first, to get them ramped up on what to do. Luckily, I leaned on my experience as a co-op back at Georgia Tech to help me lead my interns.
My biggest advice to the interns, and indeed, the same understanding I wanted them to be grounded on: “Absorb as much as you can, even if the work seems ‘simple’.”
My biggest advice to them after their time? “Re-read and re-absorb everything you did.”
One of my regrets from my internship at UPS Supply Chain Solutions back in the day was not absorbing as much as I could about logistics, transportation, the contacts I interacted with, their interests, etc. As I look back, there were hundreds of connections I wish I kept in touch with. (LinkedIn makes it much easier to do this today.)
I had my interns research our various customer profiles — their functions (i.e. sales operations, sales enablement, marketing ops, other), the challenges of each persona, how our solution could benefit these individuals, etc. By the end of their time, they could rattle off what was important to each person and could write messages or communicate with each person in a meaningful way.
I feel my co-op experience gave me great insight into being a professional and working with others, especially communication. However, I missed out on some of the “tribal knowledge” because I didn’t think much about it.
For my interns, I felt it was important (as each wanted to enter some role in business) to understand the people on the other side of the table — customers, internal stakeholders, etc. I wanted them to understand the WHY of each task. These interns were very bright, hardworking, and self-starters.
They will run up against many other students who are just as bright, hardworking, and self-starting. What will set them apart is their ability to immediately contribute and have accelerated growth. It’s this tribal knowledge, these concepts around understanding audiences, etc. that will make these interns highly valuable as they seek their next opportunities.
What are the pieces of advice you give to interns? How have you helped nurture interns? If you were an intern, what was some of the best advice or best take-aways from your experience?