Inside My Brain

Thoughts about startups, tech, marketing, and life

TAG: Startups

I saw a therapist today for the first time

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


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.

The life of a startup founder – when little things are big deals

Head in Hands

Here’s a little story about how warped my brain is from entrepreneurship, the roller coaster ride that being a startup founder is, and how my idea of a “win” has drastically changed.

Over the last couple of months, I’ve been doing customer development for my startup, WinOptix. I’ve spoken to over 30 government contracting business development folks to learn about their problems with the BD process and pitch my concept to get feedback.

I learned so much about the government contracting industry and received a ton of great feedback.

And to my surprise, one of these interviewees (let’s call him Victor, not his real name) said that he would pay to have a tool like WinOptix built!

(Yes, I definitely got excited about this at the time, but that isn’t the situation I’m writing about in this post.)

I told Victor I would get back to him soon. I hadn’t even incorporated the company nor did I have the ability to build the product, so I had to get to work on both fronts before moving the potential engagement forward.

At the same time, I was setting up my new WinOptix email address with Google’s G Suite. I emailed Victor from that new account.

Usually I would set up email forwarding to my primary email address so I can manage everything from one account and not have to check multiple inboxes. Except I forgot to do so this time.

Of course, Victor emailed me to set up a time to chat about moving forward soon. And I didn’t receive the email until I checked my WinOptix account much later. UGH.

I replied with an apology. No response. I emailed him again. No response. And again. No response.

I was totally bummed out that I might have missed out on the first paying customer because of a stupid email setup mistake. This could have been huge for WinOptix, and I just banged my head on the wall about how dumb I was and how I screwed up a massive opportunity.

I couldn’t stop thinking about my screw up and how I might have missed out on my first customer. I actually had some trouble sleeping and was down on myself for a while.

After a couple of weeks, I made a last-ditch effort and gave Victor a call.

To my surprise, he picked up the phone! He said he saw my emails and was planning to respond, but had been so swamped that he didn’t have time. And he said he was still interested in working together on the product, and will reach out soon.

I was ecstatic, just because of a simple phone call.

I didn’t even get a firm commitment, but the simple fact that the potential deal was still alive and that I didn’t totally screw it up was a big win to me.

I thought about how this situation – an email setup snafu, a missed email, then the redeeming phone call – is such a small, insignificant blip in the big picture.

But the impact that it had on me was profound.

Then I thought about a couple of things:

  1. Is this relatively small situation having such a major impact on my psyche a good thing for me?
  2. Is my reaction to this situation a telling sign of my ability to be an entrepreneur? Do I need to be more even keeled and steady, and not get so high when good things happen and so low when bad things happen?
  3. Do other early-stage entrepreneurs feel the same way?
  4. What does this situation say about my attention to detail?
  5. If I worked for a larger corporation, what would be an analogous situation, and would I feel the same way?

I’ll write more about these thoughts in future posts. To be continued…

What do you think about this situation? Did I overreact? Have you been through something like this – where a small situation has a profound impact on you? I’d love to hear your thoughts.

Photo courtesy of Alex Proimos on Flickr

The Need-Want Gap: What Companies or Industries Need, They May Not Want

mind the gap

Those on the outside might see things that companies or industries need to improve and innovate. Those on the inside may not know they need these things. If they do, they may not want them.

That’s what I call the “need-want gap.”

A great example of this is portrayed in the book and movie Moneyball.

Because the Oakland Athletics couldn’t compete with other big-budget baseball teams for top players, general manager Billy Beane had to change the way players were scouted for the team to be competitive.

So Beane eschewed “gut feel” when scouting players and looked past traditional statistics like batting average, runs batted in, and stolen bases.

Instead, Beane focused more on advanced metrics such as on-base percentage and slugging percentage to scout and recruit players and find diamonds in the rough. He realized that these statistics were more important to winning than the traditional stats, which were more about vanity.

This analytics-based methodology, called Sabermetrics, was absolutely scrutinized, and Beane was chastised by old-school scouts and managers.

This approach is still criticized to this day, even though the Athletics have been competitive with a tiny payroll for many years, and the Boston Red Sox won a World Series shortly after implementing the system.

Many middling teams knew they needed something stay competitive, but they didn’t want this kind of solution.

The need-want gap.

This happens many other industries as well.

Large businesses that have been around for many decades plod along with their traditional products and business models while startups disrupt them. Many deny the fact that they are being disrupted. Case in point here and here.

Ambitious job seekers may see that these companies need fresh thinking and innovation, but those jobs just aren’t available because these companies are satisfied with their position and don’t want to change.

The need-want gap.

Politics and government. Energy. Construction. Media. Music. All of these traditional industries have been slow to develop new business models as technology impacts them immensely.

If you’re seeking a career where you want to make change in these old-school industries, you might find that your services and ideas aren’t welcome.

But if you’re persistent and have a vision for the change you want to enact, keep going. Companies in these industries will come around when they have to.

If you can convince them that change is good and necessary, you can shrink that need-want gap and make your mark.

I hope you found this interesting! If so, please share this article with the share buttons on the left. Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at!

This is day 37 of my experiment to blog for 30 consecutive days.

Photo courtesy of Wikimedia Commons

Quality vs. Quantity – which should you focus on?

There’s a never-ending debate between quality and quantity, especially in my worlds of marketing and startups.

It’s hard to have both quality and quantity at the same time; they have an inverse correlation.

The more you do, the lower quality your work will be. The higher quality your work is, the more time it will take for each task, and you’ll complete fewer tasks.

So which is more important?

There’s a big debate about quality vs. quantity in the marketing world.

Content creation is a key part of marketing, and many companies try to pump out lots and lots of content so Google can index all of their articles and they’ll be higher on the search rankings. Sometimes this works, but it’s a grind and can cost a lot of time and money.

Then take SEO master Brian Dean. His blog, Backlinko, garners almost 120,000 unique visitors per month and a 7-figure income. And he has only written 32 articles in just over 3 years. That’s less than one blog post per month! He writes super-long articles that have a ton of value. That’s clearly quality over quantity. Not everyone can create these very long, in-depth articles, though.

Now let’s talk about the startup world.

Conventional wisdom says to do one thing and do it well. Hone in on a single problem, research it, perfect it, create a solution for it, and focus, focus, focus.

Then there is this guy who has launched 12 startups in 12 months. He built and tested a bunch of ideas to figure out what had the most potential.

Or there are venture capital firms that make only a few investments per year but focus on industries where they have expertise. Then there is 500 startups, who is playing moneyball and investing in a large number of startups (way more than 500) to diversify and spread out their risk.

It comes down to your particular situation, your mindset, what resources you have, and what you can execute.

I think there are pros and cons to each approach and you have to find the balance of what works for you.

This is day 18 of my experiment to blog for 30 consecutive days.

Reflecting on 2015, big changes coming in 2016


Another year flies by! It’s amazing how fast 2015 went and how quickly 2016 will be here.

Here are my thoughts on how I did with the resolutions I made in 2015.

And I’m not making resolutions for 2016!

Read on…

Recapping 2015

Here were my resolutions for 2015 and how I did:

1) Publicly launch ribl and gain over 100,000 users: ribl launched, but we didn’t get close to 100K users

We launched ribl publicly at SXSW in March, but we certainly did not gain over 100,000 users.

While we worked hard to launch our app, we couldn’t keep up with the fast pace necessary to maintain and grow a consumer mobile application.

We’re bootstrapping ribl, which means that we’re funding the company with our own money. Bootstrapping a startup is hard; it’s difficult to find a balance between working for paying clients and building a product that won’t bring in any revenue for the foreseeable future.

Because we had to spend a lot of time on consulting engagements, we didn’t quite get as far as we expected with ribl. Sucks.

Rating: 5 out of 10

2) Measure more: not bad

I made a resolution to be more analytical and more frequently look at the metrics of my clients’ websites, my blog, the ribl app, and any other property that I managed.

I did spend more time on analytics and learned some new measurement tools, but probably didn’t do as much as I could.

Rating: 6 out of 10

3) Avoid alcohol for two weeks every quarter: total fail

Jeez, I totally forgot about this one. Again.

Absolute fail.

Rating: 1 out of 10

4) Be a great dad: pretty good!

Baby Maya was born on May 14, 2015 and she is incredible!

It’s tough for me to truly judge how great of a dad I’ve been, but I think I’ve done a solid job so far.

Vicky and I have been working well together to balance our schedules to take care of Maya. We also have the help of Vicky’s mother and my Mom, which has been a godsend.

Maya is happy and healthy, and that’s all that really matters.

Rating: 8 out of 10

One more thing for 2015 – launch of my podcast

Another big thing that happened in 2015 is that I launched a podcast, the Go and Grow Podcast.

At the beginning of the year, I hadn’t ever listened to a podcast. But by October, I launched my own!

It’s been a great ride so far.

My podcast has reached #1 on a few iTunes New and Noteworthy categories.

More importantly, I just love speaking with entrepreneurs about how they’ve launched and grown their companies. I’ve learned so much and have been inspired by their stories.

Looking forward to 2016

To tell you the truth, I don’t feel like making any resolutions for 2016, and maybe ever again.

I just wind up forgetting about the resolutions I’ve made and then get depressed when I write this blog post at the end of each year.

Yeah, I know, it seems like a cop out. The better solution may be to actually remember the resolutions I’ve made and stick to them, right?

Instead, I’m just going to work hard, make progress every day, and balance my career and life as a whole.

I do want to highlight some major changes that are coming in 2016.

Career changes

As I stated in my recap of resolution #1, we didn’t even come close to progressing with ribl as we hoped. This was because we lacked the time and resources to focus on building and growing the app.

The ideal situation would be for me and my co-founders to dedicate 100% of our time on building ribl or whatever product we choose to develop. But life doesn’t work that way, as we all have families for which to provide, so we need income.

So I’ve decided to join my co-founders in growing their software development firm, Thorn Technologies, where I’ll be Chief Marketing Officer!

The structure that we’ve had the past couple of years wasn’t quite working.

I consulted for Thorn Technologies for a few hours per week to help market the firm and sell software development projects. And whenever we had some free time, we would work on ribl.

Thorn Tech would grow a little, ribl would grow a little, but we would still be strapped for resources and not get as far as we’d like on either.

Now I’ll be working full-time to grow Thorn Tech faster.

The hope is that by dedicating more time to growing Thorn Tech, we’ll have a larger portfolio of projects and more robust pipeline of potential clients. This in turn will put us in a better financial situation, allow us to hire more resources to both cover our client projects and help us build a product, whether that’s ribl as it exists, ribl in another form, or something in a completely different direction.

Will this new structure work? We think it will, but who knows.

It’s clear that what we had didn’t work, so we need to try something else. It wouldn’t make sense to keep going as-is and just hope that things will get better.

So we’re going to give this experiment a shot and see how much progress we can make on the product front.

I’ll still continue to grow my podcast on my free time, and maybe even launch a show for Thorn Tech!

Life changes

With the birth of Maya, our condo is getting pretty cramped. And with Maya growing so quickly, it will only continue to get more crowded.

So Vicky and I have been looking for a larger home that will accommodate our growing family.

We’re not sure where we’ll wind up, as we have to balance our love for the city, the quality of schools, availability of houses within our budget, and many more factors.

It’ll be a lot of work to find and transition to a new place. We’re not even sure if the move will happen in 2016 but it’s certainly a possibility.


2015 was a fun but up-and-down year.

The birth of Maya was certainly the highlight of 2015. Though it’s a tough job raising a child – many sleepless nights and lots of uncertainty – it has been one of the most rewarding experiences ever.

And while I’ve had early success with my podcast, I didn’t come close to achieving as much as I would have liked with the startup, which is my #1 career priority.

2016 is going to be full of change and excitement.

I can’t wait to see how much Maya develops, and look forward to the changes her growth brings to our lives.

I’m pumped about my new role at Thorn Tech, as I do believe it will help us progress in building a product.

And I’m excited to continue working on my podcast and growing my audience.

See you later, 2015, it was nice knowing you. Hello 2016, looking forward to finding out more about you!

What changes are coming your way and what will you focus on in 2016? I’d love to hear about it in the comments!

Image courtesy of Wikimedia Commons.

Guest Post for The Good Men Project – I’m a Husband, Father, and Entrepreneur, Thanks to My Wife

Good men project image

Check out my guest post on The Good Men Project titled “I’m a Husband, Father, and Entrepreneur, Thanks to My Wife.

I’ve been a husband for over three years, and a father to my beautiful baby girl Maya for just over six months. Of course, I couldn’t be a husband and father without Vicky.

I’ve also been an entrepreneur since July 2012. I owe that to Vicky as well.

Being a husband and a father were inevitable. Being an entrepreneur didn’t have to happen. But it did, and I couldn’t be an entrepreneur without the financial and emotional support from my wife.

Being a husband, father, and entrepreneur all at once takes a lot of sacrifice and compromise, and of course, not only on my part. Vicky arguably has sacrificed more than I have, and I owe everything to her.

Read our full story on The Good Men Project.

Photo courtesy of Junichi Ishito on Flickr

3 examples of startups who innovate on business model, not just product

The startup world is hot right now and there are so many companies vying to be the next big thing. If you read TechCrunch, The Verge, or any other startup or technology publication, you’ll be inundated with content about hundreds of companies with similar-sounding solutions.

If you’re a potential customer of some of these options, you might wonder – how are these companies different from each another?

Another enterprise communication software company just launched as I write this – how will it be different from Slack, Yammer, HipChat, or the 100 other tools out there?

Sweet, another project management app? I already use two of them, so might as well sign me up for a third, right?

Someone else just built a platform where you can get meals delivered to your home – should I use that one, or Munchery, Sprig, Maple, or the 30 other options that I have?

Most of the differentiation among these companies, if any, comes from the product, which makes a lot of sense. You can see or feel the differences in product and user experience, so they have the most immediate impact on the potential customer.

But what’s more interesting to me are companies that innovate and differentiate on business model. They deliver a great product (which is a necessity), but the way they significantly separate themselves from their competition is by delivering a unique solution based on how they charge their customer, and not just the product they deliver.

Here are three examples.

Zenefits – free software, commissions on insurance sales

Zenefits homepage

Zenefits is free software that allows small and medium businesses to manage all of their human resource tasks, such as benefits, payroll, time off, and more, all in one platform. Competitors include BambooHR, Vista HCM, TribeHR, Zoho People, and many others.

It’s been labeled as one of the fastest-growing software-as-a-service (SaaS) companies ever.

I’m not expert in HR management solutions, nor have I used any of these software packages. While Zenefits may differentiate itself a bit by having a better product, that’s not the point. The way they have really innovated is with their business model.

While other solutions charge their customers based on number of employees in the company or users of the software, Zenefits gives its software away for free.

Not a free trial. Not freemium. FREE 4EVA. This is basically unheard of in the enterprise software world.

Zenefits makes money by becoming the insurance broker for all of their customers and earns commissions for any health, dental, vision, and other insurance that is sold and managed through the platform.


Venture capitalist Tom Tunguz calls this a “software-enabled marketplace” and this model, when executed correctly, can lead to dominating market positions, which Zenefits is well on its way to achieving.

Thumbtack – charge per contact, not per transaction

Thumbtack homepage

Thumbtack is a website where you can find a professional local service provider to help you complete any project such as remodeling your home, tutoring your child, or refreshing your resume.

Sound familiar? It should, as there are tons of similar sites – Craigslist, Angie’s List, HomeAdvisor, Red Beacon, and Zaarly, just to name a few.

While many of these companies charge service providers a fee per transaction, Thumbtack differentiates by charging these contractors each time they contact a potential customer.

The company initially charged transaction fees and also tried a subscription-based model, but pivoted toward the charge-per-contact model because they found that this better scaled to the activity of the marketplace and acted as a pre-screener for each potential customer.

This is a perfect example of the Build-Measure-Learn principle of the Lean Startup where companies can use a consistent experimentation process to achieve success. In most cases, companies use the Build-Measure-Learn process to make changes to its product, but Thumbtack used it to alter its business model.

With a $100 million fundraise a year ago, I’d say Thumbtack made some smart decisions.

Robin Hood – no trading fees

Robin Hood homepage

Robin Hood is a mobile app where you can trade stocks for free with no account minimums, while other online brokers such as eTrade, Charles Schwab, and TD Ameritrade charge around $10 per transaction with account minimums of $500 or more.

Robin Hood recognized that the millennial segment is a group that is largely untapped by financial services firms, and the company understood that in order to get this segment active in investing, barriers like trading fees, account minimums, and complicated tools and interfaces needed to be abolished.

With little to no overhead (as opposed to many other online brokers, who have to maintain brick-and-mortar locations and pay financial advisors and administrative staff), Robin Hood is able to let its users trade stocks for free.

The company makes money by accruing interest from users’ uninvested cash balances, and is testing the collection of interest from those who upgrade to a margin account.

This is a case of a company recognizing a hole in the financial services market, understanding its target customers, and finding a way to cater to them.


Zenefits, Thumbtack, and Robin Hood are three examples of startups who figured out a way to differentiate themselves from the competition using their business models, and not just their products.

These companies were really smart in understanding their customer really well and figuring out the best way to monetize their users.

While innovating on product is still extremely important, I really appreciate when companies can find inventive business models that works well for both the end user and the organization.

Your turn

What do you think of the above companies who are innovating on business models? Do you have any other examples who are doing the same? I’d love to hear more in the comments.

I hope you found this interesting! If so, please share this article, sign up for my email list below, then connect with me on TwitterGoogle+, and LinkedIn for future updates.

Guest blog post for CEA: 7 More Tools and Tricks for Entrepreneurs to Get Stuff Done

Check out my latest guest post for the Consumer Electronics Association (CEA) titled, “7 More Tools and Tricks for Entrepreneurs to Get Stuff Done.

In December 2013, I wrote a guest blog post titled “10 Essential Tools and Resources for Entrepreneurs to Get Stuff Done,” which highlighted 10 important resources that I use to help me stay productive.

It’s been a few months since I wrote that article, and I’ve changed and added some tools and tricks to the mix. Here are some additional resources that might help you be more productive like they’ve helped me.


I hope you found this interesting! If so, please connect with me on TwitterGoogle+, and LinkedIn for future updates.

Guest blog post for CEA: The 4 Things I’ve Learned About Managing My Psychology as an Entrepreneur


Check out my latest guest post for the Consumer Electronics Association (CEA) titled, “The 4 Things I’ve Learned About Managing My Psychology as an Entrepreneur.

Startup founders’ trials and tribulations have been written about frequently in tech and business publications and mostly focus on how brutal it is to run a company. But I believe there are many entrepreneurs like me who are in the earlier stages of building companies, where things are moving more slowly than we’d like, and just aren’t far along enough to relate.

Lack of progress can be very taxing on an entrepreneur’s psyche and confidence, and it certainly has taken a toll on mine. I’ve worked on dealing with these thoughts over the last two years and here’s what I learned about managing my mind.


I hope you found this interesting! If so, please connect with me on TwitterGoogle+, and LinkedIn for future updates.

Guest blog post for CEA: How to Validate Your Startup Idea with Online Ads

Check out my latest guest post for the Consumer Electronics Association (CEA) titled, “How to Validate Your Startup Idea with Online Ads.

A quick and relatively cheap way to validate our startup idea, Locatize, was to run online ads targeting potential users, lead them to a landing page, and see if they give us their email address to stay updated on Locatize’s progress. Here’s what we did to test the demand for Locatize and how you can test your startup idea, too.


I hope you found this interesting! If so, please connect with me on TwitterGoogle+, and LinkedIn for future updates.