Category: Life

Posted on

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

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

Candor Comes First – How to Navigate Tough Conversations

relationship, candor, truth, how to navigate tough conversations

The other day, I jumped on a call with a friend who was going through a speed bump in his relationship. Though I’m no behavioral scientist nor expert in all matters regarding relationships, I’ve been privy to cousin cases between other couples, dorm-mates and roommates, as well as startup teams. And like most people out there, I’ve been through my fair share as well.

From my own experience, as well as from being a fly on the wall to others’, a large portion of the drama starts with the time spent dancing around the elephant in the room. And the longer a pair (or more) dances, the worse it gets. At the same time, it’s easier said than done. Rationally, we know that we should start with the truth. But frankly, it’s hard for many of us, myself included, to speak the truth when we need to. And in my hesitation, I usually regress to thinking: “Maybe it’ll get better over time. Maybe he/she will just forget about it. Maybe someone else will solve it in my place.”

Though I’ve gotten better at getting straight to the point, I’ve, by no means, mastered my approach.

Last week, I tuned into Elizabeth Gilbert, #1 New York Times bestselling author of Eat, Pray, Love and Big Magic, on her recent episode with Tim Ferriss. Quoting her late lover, Rayya Elias, at the 13:48 mark of the episode, Elizabeth shares this brilliant comment:

“The truth has legs. It’s the only thing that will be left standing at the end of the day… And since that’s where we’re going to end up, why don’t we just start with it?”

The Boiling Frog Problem

As all drama goes, we end up beating ourselves and others up in the process. Yet, when the dust settles, we still come back to the one left standing. There’s a similar concept that I learned in a college business course called the boiling frog problem.

If you put a frog in boiling water right away, it’ll jump out. But if you put the frog in lukewarm water and slowly heat it up, it won’t notice until it’s too late. And for the sake of the analogy, end up dying in the latter case.

The emotional turmoil we go through in our daily lives is no exception. It’s much easier to address the problem from the get-go, then let it rot you inside out. To put it into perspective, let’s say you address the problem at the beginning. There are only two outcomes possible:

  1. It’s not as bad as you expected, and you’re able to resolve it easily.
  2. It’s just as bad as you thought it’d be (as your mind regresses to the worst case possible). And well, you get burnt, as expected. But you will come out as a stronger person than when you went in. A phoenix reborn.

In closing

In tricky times, many of our relationships have been put on the rocks. The important part isn’t the conflict itself, but how we resolve the conflict. A frame of mind where there is no blame to dish out, but taking mutual responsibility to come out stronger in finding the resolution. Mike Maples Jr, co-founder of Floodgate, one of the most successful VC firms in the Valley, once said:

“Ego is about who’s right. Truth is about what’s right.”

Photo by Alex Iby on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

An Underappreciated Way to Get a VC’s Attention

message, fundraising, investor list, how to get a VC's attention

It’s been a trying time for founders to fundraise in these turbulent times. On one end, you have investors who took a U-turn on plans to invest this year. On the other, you have investors still deploying or looking to deploy capital. The latter further breaks down into: (a) investors who are taking more calculated bets – raising the bar for the kind of startup that gets the capital, and (b) investors who find the opportunity to invest in the down markets. The latter cohort of the latter cohort seems to hold truer at and prior to the pre-seed stages among microfunds and angel groups.

The Tightening of the Market

Disregarding the investors who aren’t deploying capital anymore, it’s been harder than ever to raise. Here’s why:

  1. Anecdotally, more startups are looking to fundraise. Many have pushed up their fundraising schedules.
  2. The standard is much higher now than before. And that includes a stronger consideration for the problem you’re addressing. Is it anti-fragile? Is it recession-proof? If your numbers are down now, will they eventually ‘flip’ back on track post-quarantine?
  3. Valuations are taking a hit. Where before your startup may have been overvalued (especially in Silicon Valley), many startups are facing “more realistic” round sizes. And flat or down rounds are more prevalent.
  4. When investors can’t meet founders in-person, they’re resorting to data, data, data. Investors no longer have the luxury to benchmark a gut check over Zoom/email, as they would have in noticing micro-gestures and other situational context clues. Anecdotally, investors are spending much more time and putting much more weight on diligence than before.

And, that’s why founders, more than ever, should (re)consider fundraising strategies. This was something that I learned when I was on the operating side and at one point, working on the fundraising front for Localwise.

Much like when high school students apply for college, founders should have a three-tiered list – SMR, as I like to call it:

  • Safety,
  • Meet,
  • And, reach.

Safety

Safety investors are those that are definitely going to take the meeting. And will most likely invest in you (i.e. at the idea stage, this mostly comprises of family, friends, and colleagues, maybe even early fans via crowdfunding). Admittedly, they can only contribute small sums of money. Each check also carry little to no strategic weight on the cap table.

Meet

Meet investors are investors that will most likely take the first meeting, but you’ll need to do a little leg work to get them to invest. Many of these will most likely stick to being participants than leads in any round. They carry some strategic weight on the cap table – in the capacity of their network, their brand, or advice.

Reach

Your reach investors will be your greatest sponsors. The people who have the highest potential to get you hitting the ground running. These folks usually have crowded inboxes already. And you’ll need to figure out how to best reach them. Unless they reach out to you, you will most likely fall just short of their gold standard. But once you stget these onboard, your relationship will set you up for reaching your next milestone better than any other individual partnership. At the same time, they will be the ones who are most likely going to have true conviction behind your product, your market insight, and your team. They typically lead rounds, and carry great strategic value to your startup (i.e. top tier investors, SMEs, product leaders in your respective vertical). For lack of better words, your ‘dream girl’ or ‘guy’.

Your Priorities

When pitching (and practicing your pitch), go for a bottom-up approach. Safety, then meet, then finally reach. And ideally, by the time you’re pitching to your ‘dream girl’ or ‘guy’, you’d have refined your pitch that best fits their palate.

When prioritizing time and effort, go top-down. Since you have limited bandwidth, spend the most time doing diligence on your reach investors. Then meet. And if you still have time, safety.

Diligence and Reaching Out

During your diligence process, look at their team, their individual and collective experience. Is their partnership, especially the checkwriters, diverse? Were they former operators? Or career VCs? And based on what they have, what do you, as a founder, need the most right now? Also, to better understand the marriage you’ll be getting in to, talk to their portfolio startups and investors that have worked with them before. Pay special attention to the the venture bets that didn’t work out. Was there a break up? If there was, what was it like? How did the investor help them navigate tough times?

It’s easy to be positive and cohesive when things are working out, but how does that investor react when things aren’t going as expected?

After talking to the (ex-)portfolio founders, if you feel like they have a good grasp on what you’re working on and are excited for you, ask them for an intro. Focus on those founders who have gone through the idea maze in your respective vertical, or an adjacent one. If you’re defining a new vertical, or that investor has just never invested in your vertical, but has expressed public interest of pursuing investments in yours, ask founders who have the same or a similar business model to yours. After all, that’s going to be the kind of solid warm intro you want.

In Closing

Though there are other ways to get in front of investors (some more questionable and/or gutsy than others), including, but not limited to:

  • Warm intros from friend/mutualLinkedIn connection,
  • Cold email/DM,
  • Reaching out to a more junior team member (scout/analyst/associate/principal),
  • Presenting at accelerator/incubator Demo Days,
  • Presenting at a hot conference, like TC Disrupt or SXSW,
  • Volunteering at the same non-profit as them,
  • Auditing their lecture at Stanford,
  • Or, squeezing into their elevator (although most VC offices are pretty lateral)…

… anecdotally, it seems many founders overlook the means of getting an intro from a VC’s portfolio.

Photo by Marvinton from Pixabay

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

#unfiltered #10 Idea Journals – How to Start, Prompts that Stretch your Parameters, The “Right” Setting, Embracing Imperfection

idea-journaling, sunrise, sunset

Three weeks ago, in the prelude to this post, I mentioned the art of ideating and how I personally pursue the expansion of my creative horizons. Though I have or had other systems in place (i.e. whiteboard in the shower, pen in pocket everywhere I go, meditation), idea-journaling has been, by far, the most impactful in stretching my creative muscle.

When you start:

  • Dedicate your time to doing it daily, with no cheat days. Set aside ten minutes each day to do so.
  • Invest in a journal you love. Don’t skimp. I fell in love with the Moleskine sketchbook at first sight. Though I have graduated to the Leuchtturm1917 sketchbook now. For me, investing in a higher end journal made me more inclined to journal daily – not wanting my Hamiltons go to waste.
  • Don’t worry about completeness or complexity. A journal entry can be 1 sentence or 5 pages or even a drawing. Regardless, dedicate a minimum of 1 page to each entry, even if you only fill it in with 1 sentence.

Explore different mediums of thought. Here are some of the prompts I started with:

  • Write a short story.
  • Draw a picture.
  • Design a logo.
  • Compose a tune.
  • Jot down a recipe you think could work. And after, how would you plate this dish?
  • Create a new language.
  • Write a poem in that new language (or language that’s not your native tongue).
  • What stood out to you today?
  • Write out a conversation you would have with your role model, a celebrity, your boss, your friend. Or even what your follow-up conversation would look like with someone you talked to today?
  • How would you resolve a problem that’s plaguing you now?
  • If you could change or add one fundamental universal law, what would you change and why?
  • And, if you’re still stuck without a prompt, what should be the question or prompt you ideate with today?

Why? By exploring different avenues of creative output, you give your mind more degrees of freedom to think. Expand your parameters. That’s why multi-linguists are able to host such a vast vernacular bandwidth.

The Setting

Just like the process of idea-journaling, the setting in which you do so is equally as important. Why? You ideate best in a positive or neutral environment, when you won’t tie down emotions and biases to the environment you’re journaling in. Find your sweet spot, and make it a routine. When and where do you find yourself to be the most relaxed and/or the most creative?

For me, although I don’t shy away from ideating throughout the day, I find my mind the most expansive: (1) right after I work out, and (2) right after a good hot shower. And though rare, if the above two don’t work, I take at least a 20-minute walk, tuning into either a podcast episode I’ve heard before or a non-lyrical playlist.

Once I find peace in the preamble of my ideation “ritual”, then I settle down in a place where I feel comfortable and at home. Before the crisis, my go-to spot in the city was Sightglass Coffee on 7th. Now it’s in my backyard garden. With good lighting and a cup of chamomile or green tea.

Embracing Imperfection

My idea journals are a sanctuary for me to be imperfect. And arguably, its is where I found myself to be the most courageous. I didn’t have to cower in fear of judgment and biases from other eyes. And I can be unapologetically myself. Over the past 2 years, I’ve been lucky for that same courage to have bled outside of the book-bound acid-free pages.

If I can quote a line from the prologue of Bob Iger‘s brilliantly wicked book, The Ride of a Lifetime…

“True innovation occurs only when people have courage[…] Fear of failure destroys creativity.”

Give yourself room to fail. You’re not going to like every single one of your ideas. In fact, if you’re like me, you might end up hating 4 out of 5 ideas you have when you first start off. But keep at it. Make it a habit. And one day, you’ll notice the distribution of good-to-bad ideas shift in your favor.

If you’re anything like me, when I get stuck, take some time to look up at the jewel-studded indigo canopy above. As your mind hops between one twinkle to the next, you might pick something up in the traversal.

As you make it a habit…

Although an unintentional upside when I embarked on this journey, the endeavor is truly meditative, perpetuating a positive feedback loop of euphoria. And over time, you’ll find yourself concepting more robust and intricate ideas. Hopefully, unbounded by your situational constraints. The sky’s the limit!

Photo by Leon Biss on Unsplash

#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.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

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

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

The Third Leg of the Race

swimming, the third leg

I dedicated three-quarters of my life before I turned 18 to swimming. More than half of which I spent competitively. Although I never amounted to a Michael Phelps or Katie Ledecky, the years I spent swimming were some of the happiest, yet character-building times of my life.

I was a mid-to-long-distance swimmer – anything between 200 yards (or meters) to miles-long open-water swims in the SF Bay. By golly, the waters in the latter ‘pool’ were dirty. I couldn’t see my own hand when I reached out underwater. But I digress. As a distance swimmer, the biggest lesson I learned was how to fight the mental battlefield.

The Legs of a Race

Coach taught me to break every race down into 4 quarters. The first leg, the second leg, the third leg, and the last leg.

The first leg is comparatively the easiest. You’re brimming with energy, motivation and (potentially nervous) excitement. As long as you don’t exhaust yourself in this leg, but put in enough effort to break away from the pack, you’re golden. And in doing so, you’re going at 80% of your top speed.

The second leg is when you start engaging in a psychological battle with your competitors. Understand where they are in the race, as well as their racing personas.

  • Are they a front-half or back-half swimmer?
  • Are they a sprinter from the blocks?
  • Do they typically negative split in a race?
  • In an individual medley (IM) race, what’s their best stroke? Their worst stroke?

I typically dial back to 70% speed.

The last leg is probably the second easiest. You burn everything and anything you have in the tank. The goal is in sight – within reach. It comes down to how well you’ve raced the first three legs, and how much you trained. Effectively, it is a battle of strength – a Hail Mary. 110% speed.

Now let’s rewind back to the crucial leg I skipped. The whole reason I started writing this post.

The Third Leg of the Race

Whereas the second leg is based on ‘external warfare’ and the last leg is based on ‘physical warfare’, the third leg, and arguably the most important, is one based on ‘internal warfare’. By this point in the race, you’ve exhausted more than half of your energy, yet you’re expected to output more than when you started. You’re worn and tired. And, you can’t see the goal yet, so you know you have to save some strength for the last leg.

Yet, if you can hold this leg, it can mean the difference between a win and a loss. If you lose this leg and succumb to your thoughts, your chances of winning are slim. Quite frankly, it sucks.

So I made bets with myself.

“If I can finish this lap in 14 strokes, where I’m reaching out and scooping that ice cream just out of my arm’s reach, I’m going to treat myself to some Haagen Dazs after. One scoop for every lap I succeed in.”

“I’m going to flip turn faster than my opponents. And if I can do this thrice in a row, I’m going to get rock-solid abs when I finish this race.”

“I’m going to hold my breath till the other side of the pool, so I can smell and taste the teriyaki chicken.” *At swim meets, they’re always selling teriyaki chicken and rice for lunch. It’s greasy, super salty. But if you add some sriracha, it is a hungry swimmer’s heaven.

As you might notice, some of my bets were outright ludicrous. But it was because they were crazy that I was motivated to keep going. When there were no tangible goals, I made my own.

Why am I sharing this?

Life, seeking employment, running a business, and so much more run in the same way. After your academic career, no one really tells you what your goals are or can be. You have to make your own. When you’re job-seeking and no interviews are coming your way, you have to muster the strength to continue applying – either spraying and praying or finding creative ways to obtain certain opportunities.

In startup land, day 1 till day 365 (or even till day 730) will be a honeymoon. It’ll be the first leg. You’re hacking away by yourself or with pals on something you feel strongly about. For many, your next leg is scoping out the competition and pacing yourself.

  • Should you launch with press releases on TC, NY Times, etc?
  • Should you stay in stealth?
  • Can you continue bootstrapping?
  • Do you need to hire more people to help you out?
  • Which distribution channels are the most effective? Overlooked by competitors, but you think there’s a lucky draw in it.

And then, there’s the third leg. The leg that will decide if your adoption curve forms a hockey stick or a pitcher’s mound. You have a vague idea of where you need to go, but you haven’t hit critical mass. You’re questioning your initial assumptions. You might even be questioning yourself. Did you make the right calls? Is there anything you missed? What went wrong? Should you have just taken the job your friend offered?

But if there’s anything we’ve learned from some of the best entrepreneurs out there. It’s the ones who weather the storm – the ones who have that grit – that often make it. Being able to weather that third leg doesn’t guarantee success. But not being able to weather it is close to a sure-fire for failure.

As a world…

We’re on the third leg now.

And what we do now will decide if we win or lose the race.

Photo by chuttersnap on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

Asking for Mentorship

asking for mentorship

Don’t.

… would be my short answer.

The longer answer… I’ll start with a story.

My First Mentor

This is embarrassing to admit, but 6 years ago, I barely knew what a resume was. As a hint of my ignorance, my first ‘resume’ was 3 pages long, double-spaced, and included two lines explaining a babysitting license I got back in middle school. So, within 10 seconds of it going up, I signed up for the resume workshop. In my hurry, I signed up for the first spot with the first “critique-er” I saw.

When the fateful day arrived, he didn’t show up at our appointed time. After waiting 15 minutes and asking the workshop leads, it turned out he was stuck in the depths of traffic.

But hell, I wasn’t going to go home empty-handed. So, I went around the bustling room, catching each “critique-er” there whenever they had a break, to ask them to look over my sad excuse of a resume. By the end of the two-hour workshop, I had taken notes about the flaws of my resume from every alumni there – half of whom ran through various interview questions with me – except for one. The one I had initially signed up with.

After hearing gossip and rumors from the alumni of how brutally honest he was, I had to meet this mysterious fellow. Eventually, he arrived. And luckily, the alumni invited me to join them for a late dinner. And that night, he left me with one sentence: “If you want my advice, you better take it seriously.” Not in the sense that I need to follow exactly what he tells me, but that I won’t hear then forget it the next morning.

Over the years, I’ve truly appreciated the analytical mind he brought to temper my creative mind. His advice saved my neck saved my neck at multiple crossroads of my career. He was able see around the corner when I couldn’t – a tactical mentor. Though I didn’t use his advice every single time, I always came back to him with the post-mortem.

  • How did I use his advice?
  • If I did, what was its impact?
  • If I didn’t, what was my internal calculus for choosing so?

He never pressured me to use his advice, nor did he ask that I report back to him each time. But I did. Over the years, I’ve been there for his highs and lows, just like he has been there for mine. Before we became mentor and mentee, we realized we had become friends. Ironically, to this day, he still hasn’t seen my resume.

The Bigger Picture

You might call it availability bias, but over the 6 years since then, I’ve reached out to many people – punching above my weight class, inspired to seek mentorship. But out of all the 20+ people that I asked for mentorship on the get-go, not a single one was willing to take on the responsibility for a stranger. And rightly so. Like any other relationship, mentorship requires time and commitment. Without any precedence, it’s hard to make that decision with asymmetric information.

The Venture Parallel

Even as investors, who notoriously have to be willing to not only mentor others through “just a pitch”, but also commit dollars to where their mouth is at, each round of startup funding takes at least 60-90 days of diligence and working together, before we invest. Our goal is to be ‘the best dollar on your cap table‘.

In a literal sense, a dollar is a dollar. Whether you get it from your parents as an allowance when you were 7 years old or from your managerial salary at 27 years old, it’s the same. But, in venture, there’s ‘dumb money’ – money in its most literal sense. And there’s ‘smart money’ – money that comes with advice, resources, social and professional networks, and help.

In most cases, an early-stage founder wants ‘smart money’. In that frame of mind, you want the investor(s) that have the best networks, the best resources, the best expertise, and possibly, the best brand, at your stage of a business. So your pitch should be hyper-specific. As with any ask in the world, nothing is ever guaranteed. But, to increase your chances of a “yes”, the best founders build that relationship before they need to fundraise.

Circling Back

For any other person out there, whose day job isn’t to take measured capital risk, you’ll have to work even harder to convince someone to take that leap of faith with you.

When you ask for mentorship, or advice, in general, follow through with it. Make it known that it is valued. And, show your progress after having tried it out. No person speaks hoping to reach deaf ears. So, if you don’t think you’ll have the mental and physical bandwidth to turn advice into action, don’t ask for advice. And definitely, don’t ask for mentorship. It’s not worth your time or theirs.

As a footnote to myself and to others who may be seeking advice, even with this mindset, there’s no silver bullet. Be curious. Be mindful. And, be creative. My favorite creative ‘ask’ so far is “I will pay you to work for you”.

And to my first mentor, Happy Birthday!

Photo by Juan Pablo Rodriguez on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

The Psychological Tortoise and Hare

the tortoise and the hare, mental health, therapy, race

We’re all privy to our emotions. It’s what makes us human. And I am no exception. Like many people that I know, there have been many moments in my life when I’ve been stressed. When I felt forced to make split decisions. When I’m not rational. Only to regret my actions and words down the road. Despite it all, though I have friends and colleagues who have, I’ve never dipped my feet into therapy. Instead, after years of diligence, I found solace in other solutions to navigate through my mental gymnastics:

  • Meditation and visualization,
  • Exercise/swimming,
  • Gratitude journaling,
  • And, dream journaling.

Last week, I caught up with a founder who found her initial sanctuary in therapy – a service I have only observed from the periphery. Historically, therapy seems to have carried a negative stigma. If I were to say, “I’m going to see a therapist.”

Many people’s naturally response would be: “What’s wrong?” Subsequently, many people have used therapy and its cousins as a reactive measure, rather than a proactive one. Luckily the conversations around mental health have finally reached the limelight, and people, more talented than I am, are working to change the biases associated with mental health. Although just a comparatively small step, I’m writing this post now to help shed light to an industry that for too long has remained behind stained glass.

The toolkit of skills

“Therapy, just like any other class out there, pairs you with a set of skills to tackle the world.”

So, I asked her, “What was the most impactful skill you learned in therapy that enabled you to better react to the world around you?”

“There’s this process I learned, when in the moment, where I first identify the initial ‘bad’ cause. Then I notice and name all the colors in the room. And after I do so, then I identify the next action I would have taken after the ‘bad’ cause.”

Seeing, my perplexed look over Zoom, she elaborated, “In the beginning, I would count a lot of colors in the room. But over time, I only needed to count less. The reason… so that I could take time to think and react appropriately to situations.”

Just like I was taught to take deep breaths when Joey steals my crayon. Just like meditation isn’t inherently bad or good, it’s merely an exercise you do to channel your thoughts. If you become obsessed with negative thoughts, you will heighten you respective emotions. If you focus on more positive thoughts, you will leave with a happier state of mind.

Counting colors was that for her. And practice makes perfect, as do all skills – be it mental or physical. Our brain is a muscle that’ll only get better the more we stretch, ‘tear’, and put it through the wringer. Although now she’s “graduated” from such exercises, she still practices her mental discipline through other means, like journaling.

In closing

Too often, we regress to our instinctual emotions. The purpose of such exercises is to give time for our mammalian brain to catch up to our reptilian brain. Or, more scientifically put, for our pre-frontal cortex (PFC) to catch up to our amygdala. And in giving them time to level out the playing field, we are able to make a decision where we can minimize our regrets in the post-mortem.

I’m not advocating to throw away your emotions. Personally, on multiple occasions, I have to thank my emotions for the results I was able to achieve – from channeling anger and frustration to keep myself going in the last leg of an open-water race to embracing contentment to inspire me when writing. Emotions can be your strength or your weakness. But hopefully, in honing in the toolkit available to you, you are able to make better judgments at the many crossroads of your life. One of such tools in the toolkit may just be letting the tortoise catch up to the hare, metaphorically-speaking. Or the hare catch up to the tortoise, physiologically-speaking.

Photo by Pietro Mattia on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

Drawing Inspiration

drawing inspiration, ideas, eclipse, writer's block

On Tuesday, I had the great honor to jump on a call with someone who is both a brilliant composer and an acclaimed orchestral conductor. Though he was classically trained, he found fame in the world of video games. And I couldn’t help but ask where he draws his inspiration when composing musicality to pair with various mediums of entertainment, even outside of games. He answered simply:

“Everywhere.”

He followed up that to help him frame his ideas around the subject of his piece: “I watch a little bit, not too much to have the show or game dominate in his mind, but enough to start off.” Just a small spark to start the fire. What he said echoed in mind, reminding me of a conversation I had with another friend – entrepreneur, author, and podcaster – prior to self-quarantining ourselves. He told me: “There’s no such thing as writer’s block. It’s that desire for perfection that holds us back from putting our pen on paper. But once we let go of trying to be perfect, we can find inspiration from everything around us.”

In all honesty, when he first told me this, I thought he was being quite presumptive. Especially it was at a point in time I was struggling to find content to put out weekly. But he was right. And, as you may have guessed, that became the kindling for the #unfiltered series.

Similarly, a few weeks back, a college buddy asked me where I find my inspiration for pieces on this blog. Though I am echelons shy of the musical talent I spoke with two days ago, I offered him the path I took to get me here:

  • Practice ideating daily.
  • Talk to people.
  • Meditate and/or write in a gratitude journal.
  • Write an audience of one.

Practice ideating daily.

My brain, like your brain, is a muscle. The more I practice using it, the better it gets. The same is true for ideas. The more ideas I write, the better I’ll get. It can be one sentence. Or, it can be 5 pages. But make sure to dedicate at least a full page to each day, even if 95% of it may be blank. The point is to deliberately do so every day, with no cheat days. Personally, I spent the first 2 weeks, writing one sentence entries.

So, I invested in an idea journal. In fact, probably my best investment I made in the past 3 years. And, I didn’t bother buying a cheap one. It was a Moleskine art sketchbook. At the time, a $17 purchase plus tax. And for a broke college student, that was a sizable amount – two good meals worth. A good alternative and the one I use now is a Leuchtturm1917 sketchbook. Why? Because it forced me to use it. I realized for me, the better the notebook is, the more I’m inclined to not let it go to waste.

Although I wish this was my original idea, my professor at Cal taught me this simple, but effective strategy.

Talk to people.

When I found myself unable to grasp at any ideas (that I thought were good), I talked to people. The more obsessive they were about their passion, the better. The more (positive and negative) emotion they channel into their work, the more insight they’ll have. And, frankly, excitement is contagious.

Talk to at least one of them from this cohort a week. Take notes, follow up, and ask more questions. The last part usually more independently, depending on their bandwidth.

Meditate and/or write in a gratitude journal.

Be thankful. It’s a useful frame of mind to be in. Positive thinking helps with more expansive creativity. Negative thoughts and stress, depending on its severity, narrows down the scope of your creativity.

Write for an audience of one.

Many professional writers are taught to find a target audience and write for them. Focus on a specific segment, before broadening, if ever. My mentors taught me to take this one step further. Instead one specific segment, just one person. It’s much better to write for 1 person who I know will always love my content than to write for a hypothetical many who may or may not even like it. For me, it’s myself. When I’m writing here, I’m merely a hobbyist. I don’t have any grand goal of reaching one million subscribers (not that I’m opposed to it). I’m just here to immerse myself in the joy of writing. And if I am lucky to have affected someone else’s life in a meaningful way, that’s my cherry on top.

Photo by Jongsun Lee on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

Posted on

#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook

living to eat, fine dining

I had originally planned to write this post back in February, but when the coronavirus came crashing in 6th gear, I thought it would have been unwise to urge you, friends and family to venture beyond your doorstep. So this post fell into the depths of despair, hoping to find its way to center stage after we were on the road to recovery and when restaurants reopened.

But yesterday, over a Zoom call, in catching up with a fellow foodie and college buddy, he suggested that I still post this. Not to urge people to eat out. But as a voice to support the many struggling restaurants, cafés and bars out there – many of which include our personal favorites. Before I dive into this post, I want to explicitly note 2 disclaimers:

Disclaimer 1: As I mentioned above, this post is not written to incentivize you to go eat out now, but rather just illustrate my musings as someone who loves food. And as many other businesses are feeling the brunt of the impact in the status quo, the culinary industry is no exception. Your favorite restaurant yesterday may not exist tomorrow. And you won’t even be able to experiment with any of the below musings if we don’t put a hand out now and support them when they need us most.

Disclaimer 2: I am neither a professional chef/cook nor is my trade being a food critic. So take what I say with a grain of salt, as with anything I write. Below is merely my observations in one of my most expensive hobbies as a foodie.

Given the extravagant length of this post, here’s a TL;DR:

  • Why I don’t resort to Yelp/Google when picking a new dinner destination
    • And a couple of my favorite restaurants in the Bay Area
  • My calculus for tipping – and why there are times I choose to not tip
  • Why a notebook may be your best friend in your culinary adventures
Continue reading “#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook”
Proudly powered by WordPress