On Journaling

If you do any research on how to increase productivity or how to “win the morning”, you’ll no doubt come across the benefits of journaling. I journal myself — it has incredible benefits.

However I fell victim to an all-or-nothing mentality. For some reason I felt I had to journal at least once a day — the ideal being once in the morning and once at night. As someone with a busy schedule, it quickly becomes clear how that’s not always realistic.

Of course there’s the “you don’t have 5 minutes to spare?” argument. But a question like this requires a simplistic view of life. Sure, I could carve out 5 minutes. But often those 5 minutes are better spent on something else.

Taking that a step further … if you were to carve out 5, 10, 20 minutes for every productivity hack out there, you wouldn’t have any time left in the day for actual work or relationships.

In 2018 I’ve been working on my focus. And, as a consequence of focus, I’ve been working on ridding myself of that all-or-nothing mindset. Of the pursuit of clean perfection.

That’s taken form with my blogging. With my reading. With my work. With my relationships. It’s a reality that I couldn’t bring myself to think of in the past. But now that it is my reality — I’ve seen how freeing it is.

You don’t have to finish that book. Had enough of it? Put it down and pick up the next one. You don’t have to write the perfect blog post. Get your thoughts down and publish. You don’t have to journal everyday. When you do, you’ll find it’s great. And when you don’t — that’s okay too.

I love to journal but I now love to journal even more because it no longer feels like a chore. Something that I have to do or otherwise I haven’t “won the morning”. Now it’s something that I choose to do. Something that I enjoydoing. And you know what? My day can be great regardless of how I spent those 5 minutes. It’s a matter of how I spend the rest of it and my outlook on it all.

Ironically I started writing this blog post about journaling and how I’ve found it beneficial when I do it. Then it morphed into something completely different. And you know what? That’s perfectly fine.

Cut The Fluff

Last year I signed up for Audible. I listen during my commute and, as a result, have dramatically increased the number of books I consume.

The majority of what I read is non-fiction. One theme across many (not all) of these books is that they could be much shorter. There’s one or two strong arguments and the rest of the book is filled with stories of how that argument was applied by somebody.

Examples are useful up to a point. After that, it’s fluff. Extra filler chapters to make the book longer and pricier. I don’t need the fluff. Give me the good stuff. Cut the fluff. It’s useless and repetitive.

Now as I start to see signs of this I’ll fast forward a bit and eventually drop the book if I feel I’ve gotten the point. That’s what makes services like Blinkist popular.

In general I’m not a fan of fluff. I try not to consume it or produce it. Writing without fluff is stronger. A product without fluff is more effective. Life without fluff is just… better.

Cut what doesn’t matter. Keep what does.

Content Begets More Content

On January 1, 2018 I started writing this blog with a specific goal in mind. The goal is to “write everyday and/or publish 300 posts”.

I phrased the goal in this way because “write everyday” isn’t a well-structured goal. While that is what I’m doing and it’s a habit I’m working to form, it doesn’t set me up for success. If, for whatever reason, I have to miss a day and can’t publish a post — I’ve failed and missed that goal for the year.

By saying “and/or publish 300 posts”, I give myself room to have days where life gets in the way. And should I miss that day, that’s okay. I’m still on pace for the 300 mark and the daily ritual of writing will get me there (and likely above it).

Today is the sixth day of this ritual and I’ve already found an interesting side effect. The more I write and publish, the more I have ideas for other things to write and publish.

I wrote in the initial post (of writing)…

“It allows me to offload the top-of-mind thoughts and make room for the interesting ones hiding below the surface.”

Not only has this proven true, but it feels phenomenal. I’m more energized and stimulated mentally. It’s having the desired effect, which only motivates me to keep it up.

Investor Updates

Yesterday I wrote a company update to all of our investors. This is something I send each month on the 1st. It outlines where the company is at, what we’ve accomplished, what we’re focused on, and what we need.

I’ve come to appreciate these updates more with time. They serve a number of useful purposes.

1) Reflection.

Looking back at the previous month (or year) allows me to gain perspective about all that we accomplished. It’s easy to get lost in the weeds and continually push towards the next goal. While that’s not necessarily a bad mindset, it’s important to look back and celebrate wins. Not just because it makes you and your teammates feel warm and fuzzy inside (it does), but because there’s valuable learnings in that reflection exercise.

Each month, while setting goals, our team reviews that last 30 days. What did we do well? What didn’t we do well? We take those learnings and create specific actions that reinforce the positive and embed those learnings into our company.

2) External Communication.

Keeping investors updated is a good thing. First, it can save you redundant check-ins because curious investors know they’ll be getting the email soon anyway. Second, it establishes an open line of communication. It’s an email overview of where the company is at (often with an “Ask” in it), not only providing an update, but also creating a thread that they can reply on top of — if they can help with something or have a question. It also makes investor meetings easier because nobody is in the dark about what’s happening with the company. There’s no multi-month lapse where they’re not sure what’s been going on.

Finally, if your updates are thorough and forthcoming, they can serve as an excellent sales tool with new investors. You can forward last month’s update to an investor who is interested in the company. Not only is it a great overview but you can illustrate what it’s like to work with you as a founder and how you’ll communicate once they’re on the cap table.

3) Internal Communication.

This takes form in a couple ways. When creating the email, it’s necessary to get updates from colleagues throughout the company. It’s an opportunity to dig into the numbers, learn more about projects in progress, and hear what’s working and what’s not.

Perhaps even more important is sharing context. In my job as CEO, I have a more holistic view of our company than anyone else. I’m a bit of a curator in that way. I receive inputs from everywhere (customers, sales, marketing, product, operations, investors, other founders, lawyers, research, etc.) and my output is synthesizing and prioritizing those to create a direction for the company. It’s crucial that I share my context with our team internally. Providing them not just with the “what” but also with the “why”.

This takes shape via our weekly all-hands meeting but also through these investor updates. Each employee at our company is on the distribution list so they too can see the holistic picture and understand how our progress and status is being communicated to investors.

Perhaps I’ll share the template I use for our investor updates in a future post, if people find it useful.

New Year, New Blog

I imagine I’m not the only one starting a blog today. It’s January 1st. A day many kickoff new habits, routines, diets, etc.

I’ve also blogged before. I’ve written a number of posts for different publications over the last few years. So what’s different now? Why am I doing this?

1) To flex the muscle.

My main objective is to write more. I love to write. It’s cathartic for me. It allows me to offload the top-of-mind thoughts and make room for the interesting ones hiding below the surface. It’s also an exercise for me to better understand myself and make sense of all the information I take in on a daily basis.

2) Increasing frequency.

To achieve the above, I need to make this a habit. Something I do everyday. And to do that, I need to change my style.

3) A new style.

In the past I’ve spent way too much time editing and revising posts before publishing them. No more of that. I’m pushing outside my comfort zone and spitting in the face of the need for perfectionism. No individual or blog post is perfect. Accept that and publish.

What this also means is that my posts will vary in length. Some will be a paragraph or two. Others will be 1,000+ words like most of my previous posts. It will depend on the day, the subject, and my schedule. I’m not committing to a certain style — I’m committing to the frequency. Making the exercise a habit and forcing myself to hit ‘Publish’.

So, no, this blog isn’t for you. It’s for me. It’s to get myself in the practice of writing everyday and ridding myself of the debilitating search for perfectionism. And if, along the way, some of the posts prove to be valuable to others… then great. That’s my new definition of perfect.

2 Years Ago I Quit My 6-Figure Job To Start A Company: A Letter To Myself Then

It’s been 295 days since my last blog post.

The reason for the gap? I’ve been working.

There’s much beneath the surface of that simple headline. I’ve learned a lot in that time. And as I reflect on those learnings, I think about what advice I’d give to myself back when I started.

[TLDR: If starting a company, make sure 1) you know what you’re getting into 2) you understand your customers and the space and 3) you’ve asked yourself ‘why’. Feel free to jump to any section specifically; I know this is long.]

Rewind: Feb 2015
After entering Startup Land — I went through an acquisition, worked at a big company, and landed an offer at a startup paying me almost triple what I made just two years prior.

It was a whirlwind journey that left me infatuated with this new world; one with a never-ending list of possibilities and things to learn. I was intoxicated by the process of building something from nothing. And became convinced I needed to start my own company.

My conviction quickly turned to obsession. I had to escape my day job and make this my reality. So I took the leap. I quit my well-paid position for the wonderful compensation of $0 per year — but the career I longed for.

Fast Forward: Today
The last two years have revealed how flawed my logic was. While I have plenty of work and learnings ahead of me, if I could talk to myself two years ago, the below would be my advice.

This advice should not be construed as gospel — my views and knowledge on this journey continue to evolve. It is my hope in writing this, that the lessons learned can reach, and be helpful to, an aspiring entrepreneur who may be in a similar headspace to that of mine two years ago.

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Dear Me,

You’re young. And stupid. I come from the future — so let me school you, fool. Don’t interrupt. Just pay attention and take it to heart. You need to think about a few things…

1. The Decision To Start

I’ve heard you say, “I want to start my own company”. And I get it, I do. But let me tell you — this is extremely misguided thinking.

This thinking is derived from the romanticism surrounding startups and entrepreneurship. With success stories being glorified in movies, pop culture, and daily TechCrunch articles.

Newsflash: startups are fucking hard. Those massive success stories, while attainable, are nonetheless anomalies. Read about the power law of venture capital. Even if you go into it knowing it’s hard… I promise you, it’s harder than that.

Don’t take this pursuit lightly. If you intend to be successful (you do), you’ll need to dedicate the next 5–10 years to this single mission. Considering the human lifespan and the finite resource that is time… this is a significant investment.

You’ll need to allocate the majority of your time and, more importantly, mental energy towards this one goal. You’ll need to sacrifice money, relationships, and opportunities in an effort to will your vision into a reality.

And even after all of that… the odds still say you will fail. It’s a daunting proposition. But the brutal, honest truth you must recognize.

2. Founder/Market Fit

As a founder, you need to have an incredible passion and understanding of the market you’re in and the problem you’re solving. This dynamic, referred to as “Founder/Market Fit”, is the single most important question to ask before starting.

Again, this is an idea you’ll need to pursue for the next 5–10 years (the average acquisition is 7+ years, the average IPO is over 8). This is a market you’ll have to dedicate prime years of your life to be obsessed with.

The Takeaway: You must truly give a shit about what you’re doing. Many shits, really.

You need to care deeply about making your vision a reality. About helping the customer you’re serving and improving the industry you’re in. About the company you’re building and the people who join you for the ride.

Don’t start a company because you “want to”. Or because you “think you should”. Or because you think it will “give you freedom and flexibility” (lol).

Don’t start a company just to start a company.

Start a company because there is a problem you understand intimately and you can’t sit around anymore without solving it.

And then, still don’t start the company. Start solving the problem.

Often people fall victim to confirmation bias. They spin their thoughts and the information around them, convincing themselves that starting a company is what they need to do. They tell themselves they love XYZ industry and are obsessed with fixing it. When really they just want to get out of a job they hate or find some work/life balance.

This “grass-is-greener” point of view is easy to fall into. But you need to think objectively at what you’re trying to do and why.

Anyone can start a company. But starting a business you’re not passionate about is setting yourself up for failure. Because…

1. You’ll be thinking through and dealing with the ins-and-outs of this business every day, every minute — for years to come. If you hate it, you’ll be miserable and it will always feel like “work”.
2. If you’re not passionate about it, that means that someone else out there, who is passionate about it, is better positioned to solve the problem. Play to your strengths, favor your interests, and give yourself the best chance to succeed.

Mostly, ask yourself “why?”. Why do you want to start this company? And be brutally honest with that answer. This sort of introspection can open up thoughts and ideas you didn’t know existed before.

If you decide it’s worth pursuing, your next step should be conducting extensive research to understand the industry and the solutions available. And more importantly…

3. Talk To Customers!

I know you’re a product manager and you have great wireframes and the designs look beautiful and… no. Stop. If you’re contemplating starting a company or building a product, this is the ONLY thing you should be focused on.

Talking to customers will be highest yield activity you can spend your time on. At any stage, talking to your customers provides incredible insight, but it’s markedly important when you’re just getting started. The learnings and takeaways from these conversations will guide you on where to start and where to focus your attention.

You need to understand your customers intimately. Ideally, you should be one. Understand who they are. What problems they have. How they solve them today. And, with a big enough sample size, how you can help them solve these problems in a better, more efficient way.

After doing this you’ll wonder how you ever thought about starting a company without talking to customers first.

And lucky for you, you don’t have to quit your job or invest any money to do this. Just talk people. Call them. Write an email. Take them out for coffee or drinks. Talk to as many as you can. Be relentless — like the future of your company depends on it. It does.

Related Note 1: You may want to create a blog, instead of building software, as your “MVP”. This could be a powerful way to dive deep on a topic, understand your customers, and build an initial audience.

Related Note 2: Here is a great list of user interview questions you can use.

4. Have A Co-Founder

I’m not saying solo founders can’t be successful but it does carry unique challenges. While you won’t be subject to co-founder infighting, with a second or third founder you can: get 2–3x the amount of work done (notably in the early stage where everything is manual), apply different perspectives and skill-sets to the same problem, and have a more appealing pitch to investors (some avoid solo founders).

Perhaps the biggest reason is that the emotional ups and downs of the job can be draining. Founder depression is a real thing — something I’ve experienced myself. It’s helpful to have someone in the trenches with you, who understands the details of what’s happening. Someone who can sympathize, support, and work with you to solve problems.

5. Have A Support Network

Co-founder or not, you must have a solid support network around you. This network can take different forms and provide different types of utility. Your personal network helps take care of the emotional layer — the baseline for operating each day. Surround yourself with friends and family who cheer you on, understand the stresses and demands of your job, and can be there to talk when called upon.

A professional network is equally important. This network serves to give you honest feedback. To keep you grounded and provide educated, actionable advice. They can help you brainstorm and solve problems. They can make introductions to people valuable to your business, and help grow the network over time.

Note: Don’t forget to give back to these networks. As a rule, try to give more than you receive.

6. Thick Skin

The support networks help but only you experience what it’s like to be in your shoes every day. So you’ll need to have (or develop) thick skin.

Life as a startup founder is riddled with more downs than ups. More “no” than “yes”. And more caffeine than sleep. I can’t say it’s the healthiest lifestyle choice. Early-stage startups demand a lot of time and sometimes you won’t see immediate results.

Understand that things are never as amazing or as horrible as they seem in the moment. Keep a level head and remain focused on your mission. Be open to feedback but persist on the things you know to be true. Don’t let one meeting get you down, or another convince you that you’ve made it. Take the hits, keep pushing, and hustle on.

7. Understand Investors

Always seek to understand your audience, no matter what you’re doing. Raising money for your business is no different. Understanding how venture capital works is imperative to raising that money. While not as important as understanding your customers and building something they love, if you don’t understand the motivations and incentives driving the person across the table, you aren’t setting yourself up for success.

8. Core Values

Establishing your core values at an early stage is one of the more valuable things you can do as a founder (after research/talking to customers).

It doesn’t matter how small you are. 1–2 person companies should do this. It may seem unintuitive at that size, but trust me (I’m from the future)… take the time to define your mission and core values. The good news is — they should already be inherent to who you are and what you do. You just need to talk it out and write them down.

Not establishing your mission and core values is the equivalent of sailing in a vast, open ocean without a compass.

These will inform everything you do moving forward. Hiring. Product. Strategy. Prioritization. Metrics. Goals you set. Performance reviews…. it’s the baseline for gauging everything.

The culmination of all of those decisions is what creates your culture. And culture is created whether you craft it or not. So you might as well be deliberate about what you want it to be. There’s nothing more important about your company than the people. And culture is what determines the type of people you hire, the talented people you retain, and the success of the product/service you all create. You cannot ignore this.

9. Taking Care of You

We touched on your emotional wellbeing within the context of your business — but there’s more to it. A few points here…

Physical

Seemingly obvious, this portion of personal health is often the first to suffer. For me, I deprioritized my physical health because there was nobody holding me accountable. For everything else in my life there were people who counted on me. My health was my problem, and when days got busy (they always do), I would skip. It wasn’t until I reframed this in my mind that I started making my health a priority.

You need to be at your best for your immediate network. You need to support your family, friends, and colleagues to the best of your ability. And part of that is making sure you’re healthy, focused, and capable of being there when needed.

Reading

Think of it this way… there is an opportunity cost to not actively reading.

New ideas are formed when your brain connects different thoughts, concepts, or experiences together in your mind. Applying a theory, story, or solution that you read about, to a problem in your life… that’s where creativity and innovation live.

Reading is the avenue to get you there. If you can only pull from your existing arsenal of experiences, vocabulary, and ideas — then you significantly limit your ability to solve problems and think creatively. This also applies to organizations. Valuing and recruiting for diverse perspectives makes your team better equipped to solve problems.

Writing

If reading gives you the ammo to work with, and your brain is the weapon — then writing is the trigger. All those creative thoughts and ideas are effectively useless if you don’t get them out.

On top of that, writing has this wonderful compounding effect. It makes room for more creativity. As you begin writing, you’ll find that new ideas start coming to the surface. Getting those top-level thoughts out clears way for a whole new layer of ideas to rise up.

Make sure you write every day (morning is typically best). Challenge your brain with interesting questions and scenarios. And take time to revisit and review ideas. Reading your own thoughts from a different time and headspace can often be the same as reading someone else’s prose. It can help to place you, mentally, back in a different space.

10. Keep Learning

Understanding that you don’t know shit is one of the most empowering mindsets you can take. That’s not to say you shouldn’t be confident, but there’s an important difference between confidence and arrogance. Putting on a false sense of expertise is actually detrimental.

Fuck “fake it til you make it”. Know what you don’t know and seek to keep learning and improving. This will give you all the confidence you need because you won’t be afraid to say you don’t know something. To ask for help. To learn and tackle new challenges in innovative ways. That’s how the best get better, solve problems, and succeed.

Keep on pushing,
You +2 years

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This letter is by no means a comprehensive guide on how to start a company. It’s also targeted at a company’s super early, origin stage. Each of the above could be it’s own post and plenty of lessons simply didn’t make the cut.

The point of this isn’t to delay the action. As a startup founder, all you should be doing is taking action. But those early actions could be this diligence process — helping you understand what you’re signing up for and preparing you for success.

At a certain point there are diminishing returns — where that extra book, blog post, or phone call isn’t going to make the difference. At that point, the only way to learn more is to dive in and keep learning as you go. Entrepreneurship is like a pool in that way. Just make sure you’re not oblivious to the lessons above and you’re making this massive life decision for the right reasons.

After that… push forward and hustle to make your vision a reality. It’s on you to make it happen.

Just Start

Why getting started is your biggest obstacle

Some failure in life is inevitable. It is impossible to live without failing at something. Unless you live so cautiously, that you might as well not have lived at all. In which case, you’ve failed by default. -JK Rowling

“Where do I start?”

It’s the question that everyone with writer’s block faces. But this idea isn’t exclusive to writing. It takes place everywhere: building a business, creating a product, learning a new skill.

The trick? Just start.

Honestly I had no idea how this post would take shape when I began typing. In fact, I went through a few different topics and iterations before finally landing here. But I started, and that’s how I’ll finish.

Simply starting to type, code, design, whatever it is that you’re doing, is so powerful because it forces your brain to think. This condition we label “writer’s block” is only a block because your thought process continues to run into a wall. You’re not embarking on any exercise that pushes your mind to go beyond its initial set of thoughts. You’ve limited yourself.

The proposition of actually starting is so daunting for many people that, in the end, they never do. It remains an interesting thought or idea they once had but never pursued. This phenomena is similar to what Paul Graham describes as the “schlep filter” in his post How to Get Startup Ideas.

In short — many people don’t go after a market opportunity simply because they think it’s too hard.

But why? What’s the point? Anything worth pursuing in life is going to require effort. Once you face that inevitable reality, the prospect of rolling up your sleeves seems less like a giant task and more like a logical next step.

Getting started creates a waterfall effect in your brain that pushes you to keep at it and follow through with your ideas. Never doing so decreases the probability that you’ll succeed. Doing so and failing, or finding out it’s not worth taking further, leaves you exactly where you were before — but you’ve learned something that you can leverage the next time you start.

Michael Scott starting his own company.

The often-used quote by Wayne Gretzky is, “you miss 100% of the shots you don’t take”. It’s incredibly simple and obvious, but powerful. Yet it’s amazing how many people don’t follow it. Force yourself to take that first step. To take that shot.

For me, I brought myself to start this post. And so here I am, finishing it. What are you doing still reading? Go… Get out of here.

Just start.