Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Startups

Is the startup you’re building big or cool enough?

I think about this a lot.

Is WinOptix is a big enough idea? Is my target market big enough? Is the concept interesting or impactful enough?

A lot of this “big enough” doubt comes from reading a lot of tech and startup news.

“Startup X raises $50 million dollars and now is worth $2 billion.”

“Startup Y has $100 million in revenue with no marketing.”

“Startup Z goes public, the stock pops, and the company is now worth $5 billion.”

I need to stop reading all of crap.

The fact of the matter is that I don’t know if WinOptix is big enough yet.

Yeah, the government contracting market is really big, like trillions of dollars big. But at the moment, I’m only targeting IT service providers, which is much smaller.

Can the product be eventually sold to other types of government contractors, or additional markets outside of govcon, so that the market gets much larger? Maybe. But I don’t know. I’m not there yet.

Here’s a post from Rob Go of NextView Ventures that talks about the “market size fallacy” for seed stage startups. That post makes me feel better every time I read it. It basically says, “you don’t know until you find out.”

And the product is in such an early phase that I don’t know if it will be cool or impactful enough.

There’s been a good amount of interest from prospective customers and partners. Industry experts believe in the concept and like what they see in the product. But I won’t really know how impactful the product will be until I get more paying customers.

There’s a lot of things I don’t know. But that’s OK.

So if you’re not sure how big your market is or how impactful your product is, that’s OK too.

Maybe your company isn’t venture scale. Maybe it is. So what?

Maybe your product is in a boring industry. Or maybe it’s in a hot sector like AI or blockchain. So what?

It’s tough to stop having FOMO, but it’s necessary. It’s hard not to think about chasing the shiny object. I think about cooler technologies and products all the time. But it just takes my focus away from what’s important.

So is the startup you’re building big or cool enough? Don’t worry about it, it probably doesn’t matter.

Is it good to be your own customer?

Being your own customer comes with pros and cons.

Many startup founders and investors say that it’s a good thing to “scratch your own itch” or “be your own customer”.

By this they mean that if you identify problems that you face yourself, you’ll have a true understanding on how to solve that problem, and thus can build a great solution for it.

A quintessential example of this is Asana, a project management software tool created by Dustin Moskovitz and Justin Rosenstein. While working together at Facebook, they got frustrated with disorganized projects and lack of communication among team members. So they scratched their own itch by building an internal task management tool that they eventually spun out of Facebook into a separate company. The company is now worth close to a billion dollars.

Sure, it worked out swimmingly for Asana. But there are pros and cons to being your own customer.

Pros of being your own customer

There’s proof that a problem and pain point exists

Many startups build solutions and technology in search of a problem, and these are rarely successful. This issue is causing you some kind of pain – lost time, wasted money, or something else – so there’s proof that there’s a real problem there.

You have a deep understanding of the problem

Because you face this problem, you have keen insight into how to solve it. You’ll understand how to approach the solution and what issues to look out for.

Passion for the problem

Naturally (hopefully?), you’re going to be passionate about solving a problem that you face. The solution can have a material impact on alleviating the pain you face often, so it’s likely you’ll work harder to solve it.

Cons of being your own customer

All that sounds well and good. But there are issues that come with scratching your own itch.

You may have this problem, but not enough others do

There’s a certain hierarchy in startups that goes like this: feature < product < business.

You can build a small solution that solves your problem. But maybe it’s just a feature and not robust enough to be a full product.

You can build a full product that some people might use and pay for.

But in order to be a solvent business, you need many users and paying customers.

If you’re your own customer, this problem might be a scourge to you but may not be a big deal to enough other people to become a real business.

You may think you know everything

Because you face the problem, you may think you know everything there is to know about solving it. That is soooo soooo wrong.

This might cause you to build everything you want to build and ignore the input of your users. Or even worse, you might not ask your users for any feedback at all.

What you may end up with is a solution that is perfect for you, and no one else.

Passion might make you blind

It’s great to have passion for what you do. You’ll enjoy your work more, and it can help make you more gritty.

But having too much passion can also blind you.

If you’re so passionate about solving your problem, you might develop tunnel vision and not see when things aren’t working. You might not be able to identify that not enough people have your problem or that you’re solving it in the wrong way. And you may not be able to course-correct before things go down the shitter.

My situation with WinOptix

With WinOptix, I have a sort of hybrid scenario of being my own customer, and not.

I came up with the idea for WinOptix by trying to scratch my own itch.

While working at software development firm Thorn Technologies, we would use Maryland’s database of state and local government projects to look for potential work to bid on. But writing these proposals took a lot of time and effort, and many times we would write them not knowing anything about the customer and having no idea of our chances of winning the bid.

So I came up with the idea of a system that would be able to better predict the probability of winning these types of government contracts so businesses like ours wouldn’t waste time and resources going after projects we had a low probability of winning.

I didn’t have too much experience in government contracting, so I started doing customer development with people in the federal contracting space (a much bigger market than state and local). Their input completely changed the approach I would take to solving the problem and has been a massive influence on the product to this day.

While the initial idea spawned from scratching my own itch, I didn’t know enough about the subject matter to be confident enough to build a solution on my own. So I depend on the input of subject matter experts to inform the product development process.

I think it’s been a pretty good balance so far.

Conclusion

There are many pros to being your own customer, but it can come with some drawbacks as well.

Scratching your own itch is beneficial only if you can properly identify when it becomes a burden, and adapt accordingly.

Are you building something that scratches your own itch? What are the pros and cons that you’ve faced? I’d love to hear from you!

Is your business model minimizing financial risk for your customers?

I’ve written in the past about business model innovation, and how companies can not only innovate with their product, but also with the way they charge their customers and garner revenue.

A business model innovation that I like and have been noticing recently is one that that minimizes the financial risk for its customers. While the free trial and freemium models do this to a certain extent, some companies go even further.

There are two models that I highlight in this post:

  1. When companies provide a service first, and get paid later when a certain event occurs
  2. When companies have you pay first but then refund money if you don’t use the product in a given time frame

Here are three companies that do a great job of minimizing financial risk for their customers.

Lambda School

Studies from Georgetown University and Pew Research Center have shown that college graduates make significantly more per year, and over a lifetime, than their counterparts with no four-year college degree. That’s a comforting statistic for college grads, current students, and those thinking about attending.

But there is a lot of risk in attending college.

First of all, the cost of attending college has become astronomical.

Tuition and fees at ranked private schools average over $41,000, with some of the top schools charging over $55,000 per year. Yucky to the bank account.

Growth of college tuition

Growth of college tuition – graph courtesy of US News

So unless you have rich parents who can pay for your education (lucky you), or you ace all of your high school classes and entrance exams and get a full scholarship (smart you), you’re likely going to have to take out student loans. And these loans will follow you around forever, even if you declare bankruptcy.

Second, even if you graduate college, you might not get a job upon graduation, or months or even years after. That’s pretty terrible.

Because of this increased risk of attending college, there’s been a growth in popularity of vocational programs and coding bootcamps like General Assembly, Flatiron School, and many others that have come and gone. These programs can either be in-person or online and teach you tech-related skills like web development and digital marketing. Classes typically last a few months, depending on whether you’re a full- or part-time student.

The problem is that these programs are still pretty expensive (full-time, in-person coding bootcamps can cost up to $20,000) and you’re still not guaranteed a job after you graduate. So are these programs really solving the problem?

Lambda School has a really innovative business model that aims to minimize their students’ risk of gaining a useful education.

Lambda School provides computer science and data science courses taught live and online by instructors who have worked for the largest tech companies like Google and Apple.

The big differentiator is that you don’t pay a cent for this education until you graduate and make more than $50,000 per year in salary. At that point, you pay 17% of your salary for two years. 

So let’s say you graduate from Lambda School and get a job as a Data Scientist making $75,000 per year. 17% of $75,000 is $12,750; assuming you don’t get a raise within your first two years, you would pay $25,500 to Lambda School.

That’s less than one semester’s worth of tuition and fees at some universities.

With no upfront monetary investment.

And you already have a high-paying job before you pay anything.

That’s pretty amazing.

I’m not sure how innovative their curriculum is; live online education has certainly been tried before. It’s the de-risking of the cost of the education that’s really innovative.

I learned about Lambda School from this episode of This Week in Startups.  The founder, Austin Allred, shares a ton of info about why college tuitions have soared and why he started Lambda School.

Education is one of the most important sectors of our economy and it’s clearly broken. I’m rooting hard for Austin and Lambda School to succeed so this huge problem can be fixed.

MaxSalePrice

Selling a home is a stressful task and a lot of work.

You need to make your home look nice, work with agents, price it correctly, give tours, and much more, in a short amount of time.

In the end, you want to maximize the sales price of your home. And one way to do this is to do home improvement projects before you put your house on the market. A remodeling of your kitchen, new hardwood floors, and a fresh coat of paint can significantly increase the value of your home.

These projects aren’t cheap, though. A kitchen remodel can cost over $40,000, a full paint job can cost $10,000, and installing hardwood floors can be many thousands as well.

And you have to find trustworthy contractors and pay them upfront to do this work.

MaxSalePriceMaxSalePrice logo is flipping this model on its head.

The company will work with you and your real estate agent to figure out what improvements are needed to maximize your sale price. Then their contractors will execute these projects, and you don’t pay until you close the sale of your home, regardless of how long it takes to sell it.

Everyone wins here. You maximize your revenue from your home, your agent gets her cut of a bigger pie, and MaxSalePrice gets paid for its work.

I know the company’s CEO, Rick Rudman, pretty well. He started and sold his PR software company Vocus for nearly $500 million and was the CEO of social media software Tracx. The more he told me about MaxSalePrice, the more interesting it sounded. I think it’s a really great business model and I’m sure MaxSalePrice will be really successful with Rick at the helm.

Slack

Workplace communication provider Slack does many things really well, and their business model is one of them.

Slack has a pretty amazing free plan. You get unlimited public and private channels, 10,000 searchable messages, up to 10 apps, and much more. It’s very compelling for small teams.

Slack logoOnce you grow out of that plan, Slack can cost up to $15 per user per month.

The innovative aspect of their business model is what they call “Fair Billing Policy”, where your company will only get billed for the people who use it each month. So if an employee you’ve already paid for becomes inactive, Slack will add a prorated credit to your account for the unused time.

There are very few enterprise apps that get used by every employee every single day. Even though Slack is likely to be one of these apps, they still minimize financial risk for their customers by providing refunds for inactive users.

That’s a characteristic of a truly customer-centric company. It’s no wonder why they’re valued at more than $5 billion.

Conclusion

I really love it when companies innovate with their business models, and these three companies are doing a great job of taking care of their customers’ wallets.

It has really made me think of how to structure pricing for my startup, WinOptix, and how I can de-risk this process for my customers.

Have you seen other companies whose business models help minimize financial risk for their customers? Are you doing so for your customers?

I’d love to hear your thoughts in the comments.

It’s amazing how one person can change the dynamic of your team

Starting a few months ago, the lead developer for WinOptix, Dave, had less and less time to work on the project, so I was tasked to find another developer to help out.

On my search I went. I emailed developers in my network, posted on discussion boards, and reached out to LinkedIn contacts.

I found a remote developer (let’s call him Steve, not his real name) who looked pretty solid. He had a good resume; he interned at a high-flying Silicon Valley startup and was the CTO at other lesser-known ones. He contributed to open source projects and maintained a coding blog. He was pretty enthusiastic and friendly.

So we brought Steve on board on a part-time basis to work on some front-end styling and back-end bugs.

Steve took a little while to ramp up. We thought this was OK, since getting up to speed can take some time.

But after a while, we realized that Steve wasn’t the right guy for the job. While his code was acceptable, it was not a smooth experience working with Steve.

Everything took too long. Tasks that should have taken 5 hours took 12.

Steve did not push his code (which means sharing his code changes with us to review and merge with the existing code base) often enough. We asked him many times to push his code changes more often and while he said he would, he didn’t comply. Steve would tell us that he was going to push his code, and wouldn’t do so until 2 days later. And when he did, many times less progress than expected was made.

And there were times where we would go days without hearing from Steve.

The launch of WinOptix was already delayed, and our revised deadline for launch was impending. I was down in the dumps because progress was so slow and there wasn’t much I could do about it. While we knew a change needed to be made, we didn’t have much choice but to continue working with Steve, and we planned to do so only until we launched our v1.

In the mean time, I continued to look for additional developers to ramp up our resources after we launched, since we knew we would likely end our relationship with Steve. That’s when I found another developer, Jon, through a mutual friend. Jon agreed to help out immediately.

And Jon has been nothing short of awesome.

He has cranked out so many tasks and has achieved so much more in two weeks than Steve did in over three months. The difference has been night and day. We’re getting really close to finishing v1 and are gearing up to get WinOptix into the hands of about 15 trial customers.

When you’re a small team, every team member’s value, or their subtraction of value, is amplified.

One bad seed can bring everything to a halt. A strong team member can accelerate things quickly.

This is especially true with developers at a pre-launch tech startup. As a non-technical founder, you are so dependent on developers to help you ship your product.

In a large organization, one bad sailor isn’t going to sink the ship. There are others that may be able to pick up the slack and cover for him.

But in a very early-stage startup, where a team may have 3 or 4 members, each person has an outsized impact, for better or worse.

Right now everyone is working part-time on WinOptix, so we don’t have to go through the full commitment of bringing on a full-time employee. There’s no training we have to do, no insurance or salary paperwork to fill out, nothing like that.

But even in our experience of working with part-time employees, we can feel the impact that a bad and really good team member can have.

I now have a lot more confidence in our ability to execute. We’re cranking and can’t wait to get our v1 out into the wild.

On that note, I’ll be taking a break from blogging weekly (a little preview was when I missed publishing last week). With the launch of WinOptix, things are going to get pretty crazy soon. And I have some travel planned over the next few months as well.

I’ll certainly still blog, but it likely won’t be on a weekly basis.

On that note, see you when I see you!

What if things went right?

Prospect Theory graph

Most people believe losses hurt more than gains help.

When presented with a difficult or speculative decision, many people’s first thoughts would be about what could go wrong.

But what if things went right?

I’ve invested some money into Bitcoin, Ethereum, and other cryptocurrencies and frequently have conversations with others about this. Some of the negative things I hear are:

  • Have fun losing your money!
  • I’d never invest in anything not backed by a real asset
  • Crypto has no intrinsic value – I’ll pass

I’m not saying that you should invest in things you don’t understand. I totally get if crypto is too speculative for many, and I’m prepared to lose the amount I invested; it’s not enough to break my bank if things go to shit.

But what if some cryptocurrencies actually panned out? What if the underlying technology is the future of the internet (which I believe it is), adoption rose over the years, and thus the value of these cryptocurrencies increased in lockstep? A lot of money can be made.

There were so many things that could have stopped Uber or AirBNB from becoming a reality. Local regulations did not allow for ride- or home-sharing. Riders or travelers would certainly think sitting in someone else’s car or sleeping in another person’s home would be sketchy. And who the hell would want someone else in their car or home?

If the founding teams of Uber or AirBNB actually allowed these hurdles to stop them from creating these products, the world would be a very different place right now. We’d still be waving down cabs on the street and staying in overpriced hotel rooms.

But Travis Kalanick, Brian Chesky, and the companies’ investors thought about what could go right, instead of wrong. And these companies have changed the world.

Humans are naturally loss and risk averse, and according to prospect theory, losses have more emotional impact compared to an equivalent amount of winnings.

It’s difficult to go against human nature. It’s natural to think about what could go wrong, especially if you have a lot to lose and people depend on you.

But what if things went right?

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.