Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Startups

What’s your thesis of the best path to success?

There’s a great Twitter thread that I took part in that was started by Josh Felser, investor at Freestyle Capital. Here is Josh’s initial tweet:

Of course, with Twitter being Twitter, there was some vitriol spewed at Josh.

I jumped in, asking about my situation in particular:

 

Everyone is going to have a different opinion on how to best get things done.

Some founders – those with families, lots of debt, and other factors – will have more constraints than others and can’t fully take the leap to work on their venture. Others may choose to be more risk-averse and work on their startups on the side until the time is right to make that jump. And some may go balls-to-the-wall, leave their gigs, and just run as fast as they can to get their startup off the ground. 

There’s no one-size-fits-all approach. We all have our theses. 

Josh has his thesis about those founders who won’t quit their job until they get funding. If you don’t agree, that’s fine. Just find another investor who is more aligned with your approach. I’m sure they’re out there. 

Josh may miss out on some successful investments. And he’ll have to be OK with that.

My wife has been extremely supportive of my startup endeavors, is the breadwinner of the family, and carries the brunt of paying for our expenses. I couldn’t do this without her. 

As much as I would love to work full-time on my startup, I have to contribute to my family’s well-being by bringing in income. The time to go full-time on my startup will come, but now’s not the right time. Josh won’t fund me, and that’s OK.  

There are different paths to success, and everyone will have a different opinion about what that path is. Do what’s best for you. 

The plight of the non-technical startup founder

Tech startups are hard.

You need all kinds of people to make a startup successful.

Depending on the type of product you’re building. who your customer is (consumer vs. enterprise), what stage you’re in, and other factors, you’ll need product leaders, software developers, sales reps, marketers, designers, operators, recruiters, administrators, and many other roles.

But in the very early days of your startup, if you’re a non-technical founder, by far the most important member of your team is the software developer. If you can find one.

No matter how much you know about the industry, the user, the product features, and everything else, the software developer will be the one who can actually ship a product.

You can do all the research in the world. You can talk to scores of potential customers to learn their pain points. You can create mockups and wireframes.

But all of that doesn’t mean much if you can’t ship a product.

That’s why software developers are the rock stars in the tech startup world. They can bring ideas to fruition.

As a non-technical founder, I know that I’m at a disadvantage. My coding skills, while improving little by little, are not even close to the point where I can build an app.

I need to be able to recruit software developers to help me build my product, and I’m competing against every other non-technical founder to do so. Not easy.

Once I successfully recruit them, I need to be able to communicate my vision of the app so they can build it. And a lot can get lost in translation.

Such is the plight of the non-technical founder.

Startups are hard. And if you’re a non-technical founder, they can be damn near impossible.

Rant over.

I saw a therapist today for the first time

Yup, I went to a therapist today. First time ever.

Psychotherapy

No, I did not lie down on a couch. Image courtesy of Wikimedia Commons

Over the last couple of months, I’ve been having very odd dreams where certain scenes and scenarios repeat themselves.

There are certain buildings that I’ve never seen in real life popping up in dreams over and over again. I sometimes find myself in a vehicle on a car lift about 50 feet above the ground, scared shitless. I’m often running away from or toward something. Weird, right?

So I decided to see a therapist to discuss my dreams.

Years ago, the alpha-male version of myself would have looked at someone who went to therapy as weak and fragile, and the thought of going to therapy would have never crossed my mind.

I’m a different person now, and I think it’s because I’m an entrepreneur. For better or for worse.

My therapist said that dreams are the mind’s way of processing everything around you. Your environment, everything that you do and deal with on a daily basis, and all your fears and anxieties can be manifested in your dreams.

And that’s probably what’s happening with my dreams. The stress and uncertainty of being a startup founder is the likely cause of my weird dreams. What these dreams mean is TBD.

Whenever I speak with people interested in startups and entrepreneurship, I say that managing your psychology is the hardest part.

Many of these budding entrepreneurs and founders are really smart people who have seen nothing but success in their careers. They’ve climbed the corporate ladder, obtained raises and promotions, and haven’t failed at all.

I’ve been in their shoes before. So I warn them about how it feels when things aren’t working. And things will not work a lot. Things haven’t worked for me for five years.

I also tell them how good things feel when things do work, and how you have to celebrate little wins, as insignificant as they may be. This keeps you sane.

There’s a great post titled “The case against entrepreneurship“, where the Co-founder and former CEO of the mobile game Dots, Paul Murphy, describes how difficult entrepreneurship is. Paul describes a lonely and expensive existence full of problems, fear, and greed.

One of my favorite startup writers is Nate Kontny, CEO of CRM software Highrise. He wrote a recent piece titled “Making it personal” where he describes why he puts so much of his personal life into his content and talks about the lows as well as the highs.

This kind of content – real, raw pieces that highlight the tough parts of entrepreneurship – really resonates with me and my journey. Sure, the “how I grew my business 100% in 30 minutes” or “25 things you need to do before 5AM to be successful” articles are inspiring, but that shit gets old quickly. To the writers of these articles – I’m happy for your success, I really am. Maybe even a little envious. And you are inspiring. But I don’t just want to hear about your success, I want to learn about everything you went through, even the tough times, to achieve it.

Anyway, back to therapy.

Entrepreneurship is hard. Tech startups are even harder. I knew that going into it.

Managing your psychology is one of the most important and difficult parts of being an entrepreneur. It’s not helpful to keep everything inside and having it build up until you explode.

I’m not at any risk of hurting myself or anyone around me. Many might say that I don’t truly need therapy. Maybe they’re right. But I think talking to an objective, professionally-trained third party can help get my mind right, and I’ve chosen to do that.

Let’s see how this goes.

A look back to 2017 and forward to 2018

At the beginning of this year, I didn’t make any resolutions like “lose 5 pounds” or “work out 3 times a week.” Rather, I just vowed to be more focused, disciplined, and consistent in work and life.

Let’s see how I did, and what’s in store for 2018.

Looking back to 2017

Focus

For 2017, I pledged to be more focused on a macro level (doing fewer things better) and a micro level (focusing more on the task at hand).

I’d call this a minor win.

In 2016, I spent a lot of time working on my podcast, the Go and Grow Podcast. While I really enjoyed it and it helped build an audience, it wasn’t getting me closer to my goal of launching my startup. So I put it on hold, which gave me more time and mindshare to work on WinOptix. That was a win.

But I did and continue to spend a lot of time learning how to program in Python. Python is great for data science (which will help with WinOptix) as well as back-end and web development. While learning Python took away some time and focus away from WinOptix, I think it will help me become a better technical leader, which will certainly help the company and my career in the long run.

On a micro level, there were certainly times where I got distracted from the tasks I was working on. But overall, I was very consistent in using the Pomodoro Technique and turning off notifications on my phone to stay focused. (Just as I write this, my phone buzzed. Ugh.)

Discipline

I vowed to be more disciplined with my schedule and diet and exercise regimen.

I’d also call this a minor win.

I made it a point to schedule my tasks in my Google Calendar the night before or morning of a work day. Specifically assigning a time to execute the task and setting its duration forces you to focus on that task and not allow it to expand. Super helpful.

Overall, I was relatively disciplined with my diet and exercise, if you leave out the last two weeks of holidays. :)  I worked out about 2-3 times a week, with a mixture of basketball, lifting, and push-ups and sit-ups at home. And overall, I think I ate pretty healthily over the year. Vicky and I did do the keto diet for a while, but my cholesterol spiked, so I had to stop. So I just went back to a balanced diet.

Consistency

I’d call this a draw.

I was pretty consistent in working on WinOptix. I worked an additional 10-20 hours per week on nights and weekends to make as much progress as possible.

I mostly kept up with posting to this blog weekly, only missing weeks where I was traveling or on holidays.

Unfortunately, I don’t think I was as consistent with blogging for Thorn Technologies. Writing about very technical topics like cloud computing can be tough.

And I was just OK in staying consistent on social media and keeping up with personal and home improvements.

A draw sounds about right.

Looking forward to 2018

2018 is going to be a big year. Yeah, I know, I say that every year. But for real.

First of all, I’m turning 40! So I better figure out my life soon. :)

Next, there are a few things that I’d like to accomplish this coming year.

While I’ll continue to be more focused, disciplined, and consistent, there are a few specific goals that I’d like to achieve.

The first is to acquire at least 5 paying customers for WinOptix. We’re launching the product by the end of January, and hopefully we’ll get a ton of feedback from our initial users to make the product better to the point where they’d be willing to pay for it. Then we can really go out to the market and sell it.

Second, I’d like to complete at least 3 Python projects. I’m currently working on a Pomodoro timer and a program that takes data from CSV files, concatenates them, and runs reports on the data. So my goal is to complete those and add one more project to the mix.

Finally, I want to be a better dad and husband. While this isn’t as concrete as the other two goals, it’s still something to strive for. I think I’m doing a good job, but I can always get better.

What are your goals or resolutions for 2018?

I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at mike@mikewchan.com.

I feel like I’m starting over everyday…is that a good or bad thing?

Starting line

Ever since I became an entrepreneur over five years ago, there have been many starts and stops and ups and downs. Two steps forward, one step back (or sometimes three). The roller coaster ride is to be expected.

But what I didn’t really expect was how it feels like I’m completely starting over…every…single…day.

Not knowing anything. Researching all the time. Feeling lost. But learning a lot.

Is the feeling of starting over everyday a good or bad thing?

The good parts

Let’s start with the good.

First of all, I’m constantly learning.

There’s always a new marketing channel or tactic that needs exploration and experimentation. And even with the tactics that I’m knowledgable about, there are so many different ways to execute them to address different target customers, points in the buying cycle, and many other scenarios.

And running my startup WinOptix involves so many skills where I’m admittedly weak.

I’ve had experience recruiting in the past, but mostly for marketing roles. How do I properly assess the quality of a software developer or a UX designer? Sure, I can take a look at their GitHub or Dribbble pages. But that’s only scratching the surface. It’s tougher to discern how the person will work with you and integrate into your team, how hard he or she works, and many other factors.

I have plenty of marketing, sales, and business development experience, which has definitely helped in building software for these folks. But I’m attacking an space, government contracting, where I have little experience. So learning about the industry is a task that continuously needs to be addressed, and there’s always something new happening that I need to absorb.

I’m learning Python, and holy shit, that’s literally learning a whole new language. Some days I get it, other days it feels like I’ve never seen a line of code in my life. But learning to code forces me to concentrate and think deeply to solve problems. And when those problems are solved, boy does it feel good.

Secondly, things are fresh and I’m never bored.

Unless you count my five years of entrepreneurial experience as one job (I wouldn’t), I’ve never held a job down for more than 4.5 years. And before that gig, my longest tenure at a company was 1.5 years.

This is so millennial of me, even though I’m not one.

I’m not sure if I just get bored, if I’m not challenged enough, or both. I just need to constantly learn and do new things. That’s why entrepreneurship seems to be the right fit for me, at least for now.

Learning new things keeps my days fresh and exciting for me.

The bad parts

The first bad thing is that I often feel lost and helpless.

If you’re a newbie at anything, there are many times where you just don’t know what to do. Sure, you can research some blog posts, read that answer on Stack Overflow, or ask a colleague or friend what you should do in specific situations. But not knowing so many things can wear on you and make you feel like you’ll never be able to learn or accomplish anything.

Next, I’m becoming more unemployable by the minute.

Who the hell is looking for a marketer who has also been doing a little bit of sales, product, and strategy, while also knowing a little bit of Python, data science, and design?

While that description doesn’t sound too bad, it’s really broad. While I can go relatively deep on some subjects, I’m a generalist. And many companies want specialists with focus and depth of knowledge.

Finally, I feel that I’ve wasted a lot of time and money.

I’m a pretty educated guy – undergrad degree in Materials Science, Masters in Industrial Engineering, and MBA. But unfortunately I don’t use a lot of that education I’ve obtained.

I’m not saying I regret getting those degrees and that they haven’t helped my career at all. My engineering degrees certainly have taught me how to think logically and analytically, and my MBA gave be a broad business perspective and a strong network.

Yet I just feel that despite all my education, I’m still researching everything and feeling lost more often that I should be. Sure, I got those degrees a long time ago, and things have changed. But damn, I just think they should have more impact on my everyday work.

And shit, I’m almost 40 years old. Maybe I’m writing this blog post due to a mid-life crisis, maybe I’m just really introspective, or both. Regardless, it’s hard to see 20-somethings crushing it and making it on award lists like Forbes’ 30-under-30, as meaningless as those lists are. It’s difficult to not think back and say “Man, I wish I had known 15 years ago…”

Conclusion

There’s not much to conclude here. I’m really not sure whether feeling like I’m starting over everyday is a good or bad thing.

I love learning, and acquiring new skills will certainly help my career. But being a beginner at a lot of things doesn’t add that much value in the end.

Maybe I need more focus. But then boredom might eventually creep in. Then what?

What do you think? Do you ever feel like you’re constantly starting over? I’d love to hear your thoughts.

Where do you get your energy from?

I recently listened to an episode of The Growth Show podcast and the guest was Noah Kagan, CEO of Sumo.com and AppSumo.

The episode was primarily about how Noah was continually learning new skills and how he went about doing so.

A lot of that learning advice was valuable, but the one thing that stuck out to me was when Noah talked about the importance of finding “where you get your energy from.” He quoted a book and said that it’s not about how much time that you have during the day, it’s about how you allocate your energy towards things in your day.

I thought that was really profound.

Enjoying what you do, whether it’s work or play, is one thing. Doing something that gives you energy is on a whole other level.

At work, I enjoy marketing. But what really gives me energy is working with smart people, engaging with entrepreneurs, learning from customers, and building something from nothing.

In my free time, I enjoy watching Netflix. But that doesn’t really give me energy. What gives me energy is playing sports, hanging with my family, and interacting with my friends.

If you do things that give you energy, you’ll stick with those activities for longer, do them more often, and get the most out of them. You’ll learn more, and faster.

I thought that my dream job would be in the sports industry. My job at the Washington Capitals was an amazing gig, and I loved it and learned a lot from it.

But I also learned after a while that I really wanted to build something from the ground up, and that job didn’t really allow me to. It wasn’t so much the subject matter that was important, but the ability to build, launch, and grow something and take it from zero to one was what gave me energy.

And even though my startup career has been pretty rocky, it still gives me energy everyday.

So where do you get your energy from? And are you doing those things at work and in your free time? I’d love to hear about it.

Reps and Sets

I interviewed David Cancel, Co-founder and CEO of Drift, for my podcast a while ago. Drift just raised $32 million from top-tier investors, and he has started 5 companies. The guy knows what he’s doing.

One of the things he always talks about is “reps and sets.”

There aren’t any secrets, hacks, or shortcuts. Being consistent, putting in the work, and getting better everyday is the only way to success.

mathhub multiplier

Getting a little better everyday can be huge in the long run. Image courtesy of MathHub.

You won’t get in shape if you go to the gym twice a month. You won’t run lose weight if you’re not consistently eating healthy food. You won’t learn to code if you’re not doing it and educating yourself everyday.

Reps and sets. It’s as simple as that.

Success doesn’t happen overnight

I keep telling myself that.

AirBNB is a massive success, and it feels like they got there overnight. But according to CEO Brian Chesky, their “overnight” success took a little longer than that.

overnightsuccess

Gary Vaynerchuk talks about this all the time. The guy is absolutely everywhere today, but it has taken him over a decade and thousands of videos and articles to build his audience.

James Clear had a great tweetstorm about the amount of work that you need to, over a long time, to be successful.

There aren’t any hacks or shortcuts to success.

I keep telling myself that.

Whenever something isn’t going right with my startup or my day job, I keep telling myself to be patient.

Whenever I’m coding (I’m learning Python) and I can’t figure something out, I keep telling myself that the solution will come with time (and a bunch of research on Stack Overflow).

When I go to the gym, I don’t expect to lose my gut after one workout.

Things take time.

Of course, you always want to be able to learn faster and do more in a shorter period of time. Sometimes you can, sometimes you can’t.

Sometimes you have magical epiphanies, other times you just have to grind away until you figure it out.

All of that takes time. It ain’t gonna happen tomorrow.

I keep telling myself that.

Image courtesy of StartupTxt.com

The importance of taking time off from work

Career regret

A couple of weeks ago, a story about a woman who took a couple of days off from work to focus on her mental health went viral.

In summary, Madalyn Parker, an engineer who works for live chat company Olark, wrote an email to her team that said she was taking the next couple of days off to focus on her mental health. The company’s CEO responded, praising her for her email and stressing how important it is to take time off.

This is an ongoing issue in the startup world, where 80-hour work weeks are often the norm and considered cool. David Heinemeier Hansson, the creator of Ruby on Rails and CTO of Basecamp, completely disagrees.

In the early days of my career in consulting, I used very few of my vacation days, and the thought of taking time off to work on my mental health never even crossed my mind.

When I was working for the Washington Capitals, the seasonality of the job didn’t really allow us to take any days off between September and May (when the Caps would crap the bed in the playoffs). We would take some time of in the summer, but even then I didn’t take full advantage of it.

I thought that taking days off would slow my ascent up the ladder. If I was the hardest working person in the company, I would get promoted and get more responsibility and authority.

Looking back, all that crap didn’t matter.

Unless you have a terrible manager, no one is going to ding you for taking days off. And as important and valuable as you are, your big company will go on without you and will still be there when you return. It’s harsh but true.

But as an entrepreneur, taking days off matters more, both for better and worse.

Any day that you’re not working on your product or business is a day of progress and potentially revenue lost. For each day that you take off, your competitors may be moving ahead of you, and it’s a day where you’re just not learning anything.

But if you don’t take time off, you won’t be able to recharge and your mind will never be 100%. You likely won’t be able to make those creative breakthroughs that are so important to the success of a company. You’ll get burned out.

Quite a predicament, huh?

Personally, I’ve been feeling a lot of guilt lately. I keep thinking that I don’t do enough for my day job, I don’t do enough for WinOptix, and I don’t do enough as a parent and husband. I don’t know how much of that is true or if it’s just me.

One possible answer is that I can work harder. Dedicate more hours to my day job, stay up later to work on WinOptix, and spend more time with my family.

You can see just how impossible that is.

Hopefully it’s just all in my head. And I think some time away will help clear my mind and be more comfortable with my situation. It has to be real time away though, where I’m truly physically and mentally disconnected from work. Otherwise, it’s not really time away.

On that note, I’ll be traveling to Thailand for the next couple of weeks to attend my cousin’s wedding, hang out with some elephants and tigers, see some temples, and eat some amazing Thai food. I’ll see family that I haven’t seen in a long time, and spend time with my family exploring very different environments.

I’m going to take this time to reflect on my current situation, think about the path forward, and reset my mind. So I won’t be blogging over the next three Fridays. Hopefully I’ll come back refreshed, less guilt-ridden, and ready to kick some ass.

See you in a few weeks. And remember, go take a day or two off from work and don’t feel guilty about it. It’ll help in the long run.

Let Your Personality Shine in Your Product

A couple of years ago, the folks at startup accelerator Y Combinator put on a series of lectures called “How to Start a Startup” at Stanford University.

My favorite lecture was lecture 7, “How to Build Products Users Love“, which was presented by Kevin Hale, Founder of online form company Wufoo and now Partner at YC.

There is a TON of great information about user onboarding, customer support, and much more.

But the enduring theme that I took out of the lecture was how to incorporate your personality into your product to make it something that your users love to use.

With Wufoo, they did things like include interesting microcopy, like having “RARRR!” pop up when you hover over the dinosaur login button:

 

Wufoo login microcopy

 

 

Another example was from one of Wufoo’s customers who included some hilarious microcopy in their sign-up form:

Corkd form microcopy

 

Every time you open Slack, they’ll have an amusing message waiting for you to start your day:

Slack quote

 

Of course, you need to build a product that provides value to the user, is fast, doesn’t crash all the time, has solid design, and has all of the other baseline things that a good product should have.

But these little user experience details count a lot, and incorporating your personality into your product wherever possible can delight users and keep them coming back. It can build trust, put a smile on users’ faces, and make them feel loved.

While product designs will differ, many products that do similar things tend to feel the same. There are many online form tools like Wufoo that get the job done. But the microcopy and other details that reflect the company’s personality can be the difference in winning or losing that customer.

Have you encountered a product where you saw the company’s personality shine through? I’d love to hear your thoughts!