Two Ways Investors Measure Founder Coachability

As much as investors love founders with passion (or obsession) and grit, they also want to invest in founders who have the capacity to grow as individuals as much as their startup grows. And that boils down to how curious and open-minded they are. In other words, how coachable are they? In the past 2 weeks, I’ve had the fortuity to talk to 2 brilliant angel investors – each with their own respective formula for measuring founder coachability.

Formula #1: Assessing Peer Coachability

Last year, I shared a post about the importance of all three levels of mentorship – peer, tactical, and veteran. With the most underappreciated one being peer mentorship. For the sake of this post, let’s call the first angel, Marie. Similarly, Marie finds that peer coachability acts as a useful proxy for founder coachability. And she approaches peer coachability in a very unique way:

What do you and you co-founder(s) fundamentally disagree on?

Following that question, usually 1 of 3 scenarios ensue:

  1. The co-founders can state what they disagree on. And by follow-up question, share how they resolved that disagreement, then how that applies to their framework for resolving future disagreements.
  2. They figure it out on the spot. Better sooner than later.
  3. They say, “Nothing.” And quite possibly, the worst answer they could provide. ‘Cause that means they just don’t understand each other well enough. It’s highly unlikely that given how complex human beings are, that there can be two ambitious individuals who have the exact same outlook on life. Even twins have variations in their perspectives.

Knowing what co-founders disagree on assesses not only how well founders know each other, but also, how they’ve learned from each point of friction. Whether intentionally or not, they become each other’s coaches and push each other forward.

Formula #2: Assessing VC-Founder Coachability

Jerry, on the other hand, tests the waters by offering a controversial opinion about building a business or an insight into the industry, but one he has conviction and experience in. Then, he waits to see how the founder responds. The founder(s) can either:

  1. Disagree, and subsequently walk through where the dissent starts and offer a sequence of data and analyses as to why he/she believes in such a way.
  2. Agree, but still offer how he/she reached the same conclusion.

In either case, Jerry is looking for how mentally acute a founder is and how much room for discussion there is between them. On the other hand, the strike-outs regress to 2 categories:

  1. Disagree, and spend time trying to convince Jerry why he is wrong, rather than working to persuade Jerry to possibly see a bigger picture he might not have considered before. And sometimes, this bigger scope includes a marriage of Jerry and the founder(s) insights.
  2. Agree or disagree, but unfortunately, is unable to substantially back up their claim. Becoming a yes-man/woman in the former, or an argumentative troll in the latter.

The Mentorship Parallel

Unsurprisingly, just like how VCs use these methods to assess founder coachability, I’ve seen mentors use similar methods to assess potential mentees. Many aspiring mentees seek mentorship for its namesake – that metaphoric badge of honor. Not too far from the apple tree when people start a business or come to Silicon Valley to be called a CEO or for their company to be ‘venture-backed’. A category of folks we designate as “wantrapreneurs”.

And unfortunately, many aspiring mentees find bragging rights to be the mentee of [insert accomplished individual’s name]. Yet they don’t actually mean to learn anything meaningful, much less accept constructive criticism. Realistically, no mentor wants to go through that mess. “If you want for my advice, you better take it seriously,” as my first mentor once told me.

In closing

A great VC’s goal is to be the best dollar on your cap table, but they can’t be that Washington if you don’t let them be one. And though it doesn’t call for your investors or board members to micromanage, it does mean you are expected to be candid in both receiving and using (or not using) feedback.

Photo by Xuan Nguyen on Unsplash


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How Marriage Counseling Advice Applies to Managing Team Dynamics

marriage, relationship dynamics, team dynamics

Last Friday, I jumped on a call with my wickedly-creative founder friend. Given his cognitive flexibility, our conversations usually span a multitude of topics. And our Friday call was no exception – from product design to community management to de-stressors. Then, finally, marriage counseling and its applications in managing team dynamics.

Empirically, I focused my attention on co-founder dynamics when sharing an exercise I learned in my expedition to find the curiously passionate and the passionately curious. But I realize now that there are so many direct parallels on a broader scale to teams at large. From none other than a marriage counselor.

I want to preface that this exercise isn’t designed to be universal. And there’s a good chance it may not be useful for the situation you’re in or have been in. But nevertheless, hopefully, it can be another tool in your toolkit. So, if ever, when you do feel the need, it’s something that you can pull from your arsenal.

The Exercise

  1. Start every day gauging your individual gross energy level (i.e. motivation, excitement, emotional state) on a percentage scale with your partner(s)*.
    • * Yes, this was shared to me from a perspective that was inclusive of various forms of romantic relationships, including polyamory. Though I find it to be equally useful, when used among multiple co-founders/team members.
    • To put it into perspective, I usually sit around a 60-70%. When I’m inspired, motivated, or feel I can take on the world, I’m at 90-110%. Although extremely rare, when I’m down (i.e. sick, depressed, sad, unmotivated, stressed, in emotional turmoil, burnt out, or when I just want to regress to my shell), I’m usually at a 10-20%.
  2. Assess if you and your partner(s)’ collective energy level add up to 100% or more.
    • If one of you is feeling down, can (the rest of) you make up for that energy deficiency?
    • If I’m feeling 10%, and I just find it hard to get shit done, can my partner make up that 90% and help us as a team champion the day?
    • And let the person hovering 10% take the day off.
  3. If the collective energy just isn’t there, then the team falls on 2 types of contingency plans.
    1. Can you design a system (or if you already have a system in place) where all of you don’t have to put in 100%, but can still get things done?
      • Maybe this is the day to clean your house. Or wash the car.
      • For founding teams, maybe this is the day the whole team just does data entry.
      • For content creators, I hear this is the day to go through fan mail.
    2. Take the day off. Yes, the full day. And, no halfies. As great philosopher, Ron Swanson, once said:

“Never half-ass two things; whole ass one thing.”

  • Go take a day trip into the wilderness. Play video games. Read a fiction book. Draw. People-watch in a cafe (well, after the quarantine). Netflix-binge. Go tackle something on your bucket list.
  • And cap the downside – the potentiality of a slippery slope. I usually cap it at 3 days. Any longer, the counselor recommended seeing a relationship specialist.
    • Relationship counselor, if romantic.
    • Therapist/psychologist, if emotional.
    • Executive coach, if pertinent to co-founders.
    • Organizational therapist/psychologist, if pertinent to team.

What I didn’t realize until the Call

It seems obvious in retrospect, but it didn’t click until my buddy and I were thinking aloud. Subsequently, we realized how pertinent that exercise can be in understanding team workflows, as well as knowing when to double down and when to backpedal. Productivity has taken a sharp decline in this pandemic. For many, they’ve felt busier and working longer than before. The lack of diverse human interactions – for both extroverts and introverts – is really taking a toll. After all, we’re a social species. For managers, co-workers, and lateral teams, this exercise can be a way you can proactively assess your team’s morale and mental health. Assess early and optimize flexibly.

Photo by Sandy Millar on Unsplash


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#unfiltered #7 Words are Food – Having Empathy, Job Resources Now, Letting Staff Go, and Perspective Shifts

words are food, empathy

I jumped on a call with my good buddy, incredible founder and one of the most magnanimous people that I know, Mike, not too long ago. And no, he did not pay me to say that. As always, we nerded about everything on the face of this planet, but one thing in particular stood out to me. And inevitably manifested into the foundation of this #unfiltered post. He said, just 3 words:

“Words are food.”

The more we delved into this rabbit hole, the more robust the metaphor began. But for the sake of not running your ear off, I’ll cover just one facet of our parallel.

Compliments are sweets. They’re great in moderation, but too many give you cavities. They wrap up a great meal, but you cannot live your life only indulging in compliments. On the other hand, constructive criticism are your vegetables. They may not taste the best, but they’re healthy for you. And a healthy diet should consist of mostly fruits and veggies. Yes, brussel sprouts and eggplants too. Of course, it’s important to note that blatant criticism, like “You suck” or “You’re dumb” is garbage. They neither taste good nor are they healthy for you. You can smell it from miles away. So just steer clear.

After all, you are what you eat. 😀

Empathy in Words

In the past 4 months, we are all going through a transitory stage in our lives – some more drastic than others. Some of us have experienced the deaths of loved ones. Some, a test of relationship integrity. Others, career shifts and a change in household income. For those of you who have been affected by the job market, my friend passed me this resource which I hope you’ll find use in honing your job search. Anecdotally, it seems pretty accurate.

And almost everyone, a dietary change and restriction, due to the market’s supply and demand. And it’s more important a time than any (not that you shouldn’t when the curve flattens and the markets recover), be empathetic.

Be kind – with your actions and your words. In these times, it’s so easy to be caught up in what’s not going right in your life, but you’re not alone. You never are.

Empathy in Business Now

Although this applies to so many different aspects of our lives, I’ve found its pertinence on the business front recently. When the focus of businesses now is on cash preservation rather than growth, which I’ve alluded to in previous posts (1. cash in private markets, 2. heeding advice , 3. brand as a moat), aggressive decisions can be tough. As the saying goes, measure twice, cut once.

Here are some examples of said (preemptive) decisions I’ve seen from founders so far:

  • Reallocating 30% of the company budget to the core business from expansion and venture bets (70-20-10 rule of thumb to 100-0-0)
  • 50% cut to CEO salary, 10% cut to management, 5% from everyone else, to try to minimize layoffs
  • 100% cut to founder(s)’ salary, 35% cut to management, everyone else keeps theirs the same, while offering healthcare benefits for temporary workers/contractors

The conclusion for some founders may reach the point of laying off people who followed you believing in your dream. You can check out Mark Suster‘s, Managing Partner at Upfront Ventures, rubric for questions you need to consider in empathetic moments of business decisiveness.

Empathy won’t change decisions. The tough, but true remarks are your vegetables. People will still have to eat them, but be understanding of where the people eating the food you cooked up are coming from. Rather than boil your brussel sprouts, offer crispy ones with a soy glaze, a little heat, and a layer of bonito flakes.

Perspectives Forward

Recently, I had the fortune of connecting with a founder whose parents were refugee who found sanctuary in the states. She put things wonderfully into perspective, when comparing the current situation to the one she was familiar with as a child.

“There are 2 camps of refugees: (1) those who want things to go back to the way they were before, and (2) those who move forward knowing that life will never return to the ‘normal’ they once knew.

“And those who progress forward are those who believe in the latter.”

When the dust settles after all of this, life won’t ever be the same as it was 4 months ago. The hospitality, transportation, travel, and service industries, just to name a few, will irrevocably change. You friends and family may have lost dear ones.

Alas, I’m an optimist. And I know that we’re going to come out stronger than we were when we went in. We’re going to have to get used to a new diet. I dare say, even a new vernacular.


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


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Setting Culture

Photo by Aron Visuals on Unsplash

I just started my second read of Ben Horowitz‘s new book, What You Do is Who You Are: How to Create your Business Culture. It’s a brilliant deep dive on what culture and virtues mean for a growing company or team. From the most successful slave revolution in history to prison culture to the samurai bushido, Ben draws parallels between those and startup culture, where you can get a snapshot here.

On page 31, Ben wrote “Create Shocking Rules.” Why “shocking”? So people will ask why. So people will pause, think, and remember them. What is “shocking”? In a time when raping and pillaging was the norm, Toussaint Louverture, the man who led the Haitian Revolution, forbade officers from having concubines. And he kept to that promise. When “shocking” isn’t the only game changer, you need uncompromising commitment to those rules. Weak follow-through is another fallacy in creating the culture you want. What you let slide will define the new culture, with or without your approval.

Sun Tzu and the Concubines

Rereading about Toussaint Louverture reminded me of a story my dad used to tell me by my bedside. About another brilliant general, who lived 2000 years prior to Toussaint during the Spring and Autumn Period, and best known for authoring The Art of War, Sun Tzu.

Through his thirteen chapters, dubbed The Art of War, he eventually earned an audience with the king of the State of Wu. Hoping to test Sun Tzu’s strategies to its extremes, possibly expecting to see Sun fail, the king asked Sun to test it on his harem of concubines.

After accepting the task at hand and separating the concubines into two companies, Sun had them all take a spear in hand and said, “I presume you know the difference between front and back, right hand and left hand?”

The women answered, “Yes.”

After explicitly explaining what “Eyes front”, “Left turn”, “Right turn”, and “About turn” meant, he issued his first order at the sound of the drums, “Right turn.” But, the concubines responded with fits of laughter. Sun Tzu proclaimed, “If words of command are not clear and distinct, if orders are not thoroughly understood, then the general is to blame.”

In another attempt, he called out, “Left turn.” His words met the same fate as the ones he uttered just prior – with laughter. This time, he said, “If words of command are not clear and distinct, if orders are not thoroughly understood, the general is to blame. But if his orders are clear, and the soldiers still disobey, then it is the fault of their officers.”

Subsequently, he ordered the heads of the two companies beheaded, whom happened to be king’s favorite two concubines. Seeing what had unfolded from his pavilion, the king sent a messenger to plead with Sun to keep his two favorite alive. But Sun did not relent.

After their execution, he immediately installed two new officers, and from then on, the concubines followed every order that Sun issued to the T.

Using the principles he shared and taught in The Art of War, Sun Tzu won many battles for the State of Wu, most notably, when Sun Tzu led an army of 30,000 to defeat an enemy numbering ten times more than the troops from Wu. As Jon Stewart, former The Daily Show host, once said:

“If you don’t stick to your values when they’re being tested, they’re not values: they’re hobbies.”

In Closing

In his book, Ben shares quite a bit how some of the best leaders in the world shaped their organizational culture. It wasn’t from catered lunches or having dogs in the office every Friday. Culture comes down to setting “shocking” rules, paired with a set of priorities, and more importantly, keeping them. Culture is what your team members remember about your organization and how it made and makes them feel 20 years down the road.

Though not perfect, my former swim coach instilled the same virtues in us. He was never a fan of tardiness. To him, it demonstrated a lack of character and commitment. And to enforce that, if we were late, by even a minute, to get into the water (not arrive at the pool), the offenders had to swim the entire warm-up in butterfly – the whole 2000 yards. And not one person escaped that law, not even him – not that I ever saw him late.