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.

Continuing last Thursday’s post on two entrepreneurs working with two inexperienced developers early on… The devs are experienced programmers, but just as important, they’re inexperienced in early-stage startups.
The problem for entrepreneurs isn’t finding early partners… it’s finding the right partners. Finding partners (of any functional resource) who will fight it out in an early-stage startup to get to product-market fit and beyond is tough.
The entrepreneurs in the presented cases should manage expectations of the dev partners as soon as possible – set expectations the road ahead will be long and tough.
In both cases above, the devs will not work full-time, and they want equity as a discount to cash. The problem is that early-stage startups need iterations to launch, learn, build, and repeat – most will struggle to find meaningful traction before product-market fit which could take 18 months. As that happens, passion and patience will be tested on both sides – the entrepreneurs and the devs. Lack of traction can dishearten anyone, especially those working late into the night on a project but not seeing “meaningful” shifts in customer acquisition, yet.
A recurring piece of advice I’ve heard over the years from mentors (during Body Boss and every business since) is having an operating/ partnership agreement before any partnership moves forward. You can go further in a contract by detailing deliverables and compensation (outright payment, equity, or mix of both). Here, contracts could include incentives for achieving milestones to ensure all parties stay committed to the cause while including opportunities to sever relationships if needed.
To be honest, contracts suck and can be deterrents for some partners. However, they can play critical roles later in light of success and failure. If individuals do want to move forward as partners, they’ll appreciate the importance of contracts.
Early partners are very tricky, and there’s no formula on the right one(s). There’s a mixture of trust, personality, can-get-shit-done attitude, and grit to overcome obstacles – each hard to measure. But if the entrepreneurs above are serious about their ideas, they need to be cautious bringing on inexperienced early partners.
What are some other areas to be cautious of with early partners? How would you qualify and move forward with an early partner?
I was speaking with a friend about what he’d seen in venture capital on what makes an entrepreneur. We talked about how entrepreneurship is about execution – “ideas are nothing if they remain as ideas”, except, there’s a wrinkle here.
Thinking about several others who have “started” an idea or launched an app, I don’t qualify them as entrepreneurs yet. Heck, I started Dee Duper in Dec 2014, but did nothing to sell it once it launched.
Many have grand technology ideas and can hire others to build them. Once built and launched, are these owners also entrepreneurs? Not immediately, no. They’ve launched somethingand they’ve funded it, but I wouldn’t qualify them as entrepreneurs yet. 
So what makes a true entrepreneur? There’s a myriad of actions and decisions that may qualify them, but I’m going simple to say, “Sustained execution”.
Just because I golf a few times a year doesn’t make me a golfer. If someone runs twice in a month, I wouldn’t qualify him as a runner. He goes on runs, but he’s not a runner. Entrepreneurship is similar. It’s about sustained execution. It’s about meeting the needs of the market, developing and delivering some solution, and iterating the idea to serve the market… continuously.
During the tribulations of Body Boss, my cofounders and I were entrepreneurs. We were activelyiterating our product months after launching. I met with prospects and helped customers daily. We attended tradeshows and sold our product to the masses. And of course, we struggled, too. Entrepreneurship is about the ups and the downs. It’s about persistence and sustained execution.

What are your thoughts on entrepreneurship and sustained execution? What about execution in general?
I had lunch with the Founder of one of the startups I’m working with and the company’s CEO. The Founder is the visionary, and ran the business for the last several years. Early this year, the Founder tapped the CEO from the outside to take over the company’s day-to-day.
Normally, the CEO role encompasses strategic and visionary activities; however, in this case, the company Founder continues the strategic duties. The CEO is the “scaler”.
I sat down with the CEO privately to ask him what being a scaler meant to him:
  • Does not need to be the one with the original idea. Instead, he embraces ambiguity in the direction of the company, and is excited for the opportunity to grow (scale)
  • Instills processes to complement startup scrappiness with structure. The startup, in this case, has product-market fit, revenue, and a sense of the future direction – prime opportunity for a scaler. As an early-stage startup, processes are more machine gun spray. With maturity, the scaler focuses the company on a clearer target
  • Supports structure by promoting and hiring the right team members. The scaler identifies non-contributing links and removes them while filling gaps with trusted colonels from outside or promoting from within
  • Balances the values and ethos of the startup with structure and governance. As a company starts to scale, structures will develop to support growing lines of communication, product development, marketing and sales, etc. Delegation and accountability is shifted to provide effective lines of leadership and support

Some entrepreneurs thrive on building companies from scratch but are less interested at some level of maturity. For the benefit of the company and its stakeholders, it’s important to realize the gaps in the team via the management team or simple self-awareness. Then, augment the team with complementary leaders to grow efficiently.

What are the benefits of having two leaders at the helm of a startup in the early growth stage, each leading one of vision or day-to-day? What are the dangers? How could scaler entrepreneurs play roles in early-stage startups?