A Startup Journey: Deciding To Take The Journey

Photo by Casey Fyfe on Unsplash

Series Overview

Almost two years ago (well, around 688 days ago, but who’s counting…), I left my job as a Data Science Manager and started a company, Next Mountain.

I did this with eyes wide open — in addition to having a relatively strong technical background and experience, I have an MBA and have worked with early stage VCs and entrepreneurs.

While the company has yet to become a raging success, I have learned so much over the course of the experience that I wanted to share some of the journey with the entrepreneurial and developer communities.

More specifically, writing this series is my attempt to give back to the myriad of people (entrepreneurs, developers, VCs, academics, and many more) who blog, publish videos, write software, create courses, and otherwise share their knowledge with the world, as well as to pay it forward to the next generation of entrepreneurs who will strive to change the world for the better.

So, this blog series essentially aims to be an elaborate thank you to many people, in its own way.

And, it’s important for entrepreneurs to note each of the resources that I mention, since they are extremely relevant to building a startup. Just as these resources help challenge the status quo in fields like education and software engineering, providing you with the capabilities and knowledge to succeed, they also help challenge the antiquated homilies and contradictory misinformation that you’ll hear when you build a company.

Thank You, Fellow Developers

To elaborate on what I mean regarding developers, these posts are my attempt to give back to the many outstanding members of the open-source software community, many of whom may be interested in starting a company at some point in their own careers.

There are too many fabulous projects to call each one out specifically, and I really don’t want to call one out and leave another one out, but let’s just say that I still get excited when I’m integrating a new and interesting capability into a product and the process is made just that much simpler because of a nice, well-written, and beautifully-tested package that someone, or some team, somewhere, decided to share with the world.

For years, I have felt remiss in not getting more involved with open-source software. Many of these projects facilitate global innovation, which is something that I care deeply about. And, there are so many fantastic projects that I’d like to contribute to, in addition to some that I’ve been considering building. But in the meantime, I’m going to write this blog.

Thank You, Educators

I also appreciate the hard work that many academics and experts put into building online courses, or even just sharing their course materials online. For example, you can find a wealth of information in MIT’s OCW and from so many other great universities on iTunes U (increasingly hard to find now, but here’s Stanford’s), edX, Coursera, Udacity, Stanford Lagunitas, Stanford Engineering Everywhere, and so on.

You can also find some great courses on Udemy, frequently taught by industry professionals, though rarely free. Local technical and trade schools are also excellent sources of knowledge, often at affordable prices.

In fact, I’ve participated in many MOOCs to acquire knowledge and skills, starting in 2011, and I have used that knowledge directly in the workplace and in life. Certificates mattered less to me than the skills derived, so I completed some courses and dipped in an out of others.

As you might already surmise, I am a huge believer in global education and lifetime learning, for many reasons, and it’s exciting how the field continues to progress, and how universities like Stanford (I’ve taken graduate courses and earned a graduate certificate through SCPD) and Georgia Tech have challenged and extended the traditional educational model.

Georgia Tech deserves a lot of credit for going all-in on online education — no let’s-dip-a-toe-in-the-water dabbling — the Georgia Tech faculty and administration is not afraid to learn the gotchas, while constantly striving to deliver outstanding content at an affordable price, in a way that provides more access globally, without cannibalizing their own program. I have completed some of Georgia Tech’s CS courses, and the content is outstanding. Well done, Jackets. Well done.

Of course, many universities feel strongly about educating more broadly, such as when my doctoral alma mater, a public university with limited funds and a school that I have a lot of love and respect for, made a great number of courses freely available several years ago. I was deeply saddened by this news, where a lawsuit led to over 20,000 video and audio lessons from that school being deleted from public access.

I understand the lawsuit, sympathize with the plaintiffs, and love lawyers as much as the next guy does, but isn’t there a better way?

Do we have to throw the baby out with the bath water?

Couldn’t people come together and crowdsource transcripts and subtitles?

Sometimes in MOOCs, students translate material into their primary languages, and these translations are added as transcripts and subtitles. That’s outstanding.

Subtitles aren’t mystical. When I developed a course, I spent days adding captions, so that I could launch it with CC, because I thought that was important. It’s painful, but the work can be distributed.

Or perhaps someone could automatically transcribe and/or subtitle the content, then edit it? YouTube does a good job with automatic transcription.

No one had the bandwidth for that?

No one wanted to learn the material that much deeper?

No one wanted to do something good for their fellow lifetime learners?

No one sought funding or a grant for it?

Maybe I missed those efforts, and maybe things were too late by the time of the trial, but I didn’t miss the article mentioning the deleted content.

Note to self: find copy of Fahrenheit 451 and schedule reading session…

But I digress.

Before we move on, I’d like to continue encouraging those educators who push through technical roadblocks, overcome political battles that don’t make the six o’clock news, support each other, interact with students at a global level, and generally help push humanity forward. You’re doing something that is deeply meaningful and important.

Thank You, Fellow Bloggers And Authors

Of course, people blog for many reasons, but I only judge the quality of the content. It takes a lot of work to produce something that you’re ready to show to the world. It’s amazing how irritating it is to find that you published a typo.

I’ll point out a few good blogs, although linking to these blogs doesn’t mean that I agree with everything in them or even endorse anything in them. Something tells me that some of the authors may not even agree with me. And that’s OK — things change with time, and others’ interpretations of data and experiences may differ from mine.

For example, I’ve read most all of Paul Graham’s essays, and his posts contain some extremely good advice for entrepreneurs. While PG seems to be on an essay-writing hiatus (hopefully, he’s busy writing a second edition of On Lisp or gearing up for an epic Tweetstorm about Life, The Universe, And Everything), you can find additional quality content at the Y Combinator blog.

Several other investors produce helpful articles for entrepreneurs, such as those by Brad Feld, Fred Wilson, and Mark Suster. Marc Andreesen also has some solid content in his blog and on Twitter, but the volume has slowed recently. Hopefully, this hiatus is transient.

And of course, we shouldn’t ignore the many great and helpful entrepreneurs and technologists who blog, either. For example, Jacques Mattheij recently dissected the “nightmare GDPR letter,” offering thoughts for entrepreneurs who are being targeted by those attempting to take advantage of a well-meaning but sadly ripe-for-misuse-and-abuse law.

There are so many others that I should mention, such as Hiten Shah and Andrew Chen, who is also found on Facebook. But you’ll get to know them as you spend time researching, reading, and engaging with them.

Additionally, we all know that books are not usually free (well, you could go to the library, and Larry Kim mentions some resources including free books here…), but they also take a lot of work to write. I find that a good book frequently more than pays back its cover price, and I’m happy to purchase a book by an author who has written a great book that challenges my thinking and teaches me something that I want or need to know.

There are tons of books for entrepreneurs, and it’s worth exploring those authored and recommended by Steve Blank.

I’ll also mention one book that I’ll bring up again later, The Founder’s Dilemmas, by Noam Wasserman (sadly, his blog isn’t currently responding, but his book is well worth the read). I’d put this book in the “required reading” category for founders. Yes, it’s somewhat academic, but it’s also very practical and data-based.

Investing the time to read books and blogs can save you a lot of heartache later.

Internal Motivations

On the more personal side, I wanted to reflect on the journey even deeper than I normally do, and writing has a way of helping me reflect more deeply.

For example, as you might imagine, the journey includes both successes and failures. As I typed that sentence, I didn’t want to write “failures,” and I felt some resistance as I typed it, but that’s just dancing around reality. Of course there have been some failures. Writing about experiences has a way of forcing honesty with myself.

And much of the payoff of the entrepreneurial journey isn’t financial — there may never be a financial payoff. It’s in the experiences. It’s in the perspectives. And it’s in my own personal evolution.

In those respects, I’ve gained immeasurable wealth.

And that journey isn’t over.

What To Expect In Terms Of Content

I have already given you some clues about where we’re going, but let me give you an idea of how this series will likely unfold, so that you can decide whether to join me on this journey, or perhaps to go back to your Friends marathon and preparing for the upcoming show.

Mainly, you can expect honesty — not just saying things that are true, but saying things that I have considered and questioned for myself at a deep level. I mentioned that this series is a thank you, but that doesn’t mean that tough love is thrown out the window. That’s the baby.

I’m aiming to give you an unvarnished look at starting a company over the past two years, including both business and technical aspects. I’m also aiming to share a lot of the lessons that I’ve learned over that time.

For example, on the technical side, off-the-shelf technology has advanced to the point that a single developer of average skill can build apps, deploy changes, and scale the apps to meet demand reasonably well. But, there are a lot of details to consider. So, we’ll discuss a lot of those enabling technologies, including some of the finer points around them. And, I’ll strive to keep my opinions balanced.

Naturally, it’s not all success and glory. Where was I wrong? Where did I delude myself? What could I or should I have done differently? I’ll try not to armchair quarterback myself, but I’ll admit some of my failures.

Of course, I may also be wrong in some of my conclusions. Being wrong happens in science, and it happens everywhere. It’s even happened to me before, as you’ll soon see below.

So, there’s that. But, I’ll try to point out the uncertainty in my conclusions, where appropriate.

You May Experience Controversy

I don’t intend to embarrass or otherwise criticize anyone, and I take pains to avoid doing so. I may state that I disagree with someone or some entity, but there is no malicious intent (don’t worry, I paid attention in the constructive confrontation class that I was required to take at Intel).

And that clearly doesn’t mean that this is going to be a rah-rah series of fluff posts. I don’t believe that progress comes from everyone agreeing with everyone else. Realistically, that would be more harmful than honesty, as we would wallow in groupthink and other ills.

I promised you honesty and thorough consideration earlier in the post. What’s that founded on?

My background includes an MBA and an undergraduate degree in psychology, where I engaged in a year of Honors social psychology research focused on repression-sensitization, with one of the coolest professors ever. Based on these qualifications and experiences, as well as years of reading and reflection, I’m reasonably well versed in mental heuristics and cognitive biases.

I also hold a PhD in the hard sciences from a university and research group known for academic rigor, so I hold myself and others to high standards. I always consider the evidence for any conclusion proffered (experience getting burned also compels me to do this). Moreover, I’ve worked in analytical and data-related roles for a long time, as well.

Realistically, when you think about it, you’ll have to agree that it’s amazing that people’s minds can make sense of the innumerable pieces of information impinging upon them each nanosecond. I mean, think about what your senses must be perceiving right now, just to make sense of this blog. That’s hard to argue and hard not be amazed by.

But, in dealing with all of this information, the mind filters and transforms it, in somewhat different ways for each person.

For example, have you ever been offended, and the other person not know why you’re offended? Or have you offended someone, but you can’t see why? Or maybe you had an argument or disagreement with someone who just wouldn’t see your point, no matter how hard you tried?

Somehow, and somewhere, reality isn’t being shared.

Thus, I consider how these mental processes affect people’s views of reality and the resulting conclusions that are drawn.

I also consider each author’s or source’s personal incentives, which may consciously or subconsciously affect their statements.

So, considering all of this, you might find that some of what I say may be a little bit controversial. Or more than a little bit.

You can find many great examples of questionable assertions and wastes of time in the startup space.

For example, in my opinion, in addition to worthless, content-free drivel hiding behind clickbaity titles that only serve to drive ad views, there is a great deal of outdated crap founded on a mountain of anecdote-laden guesswork and extrapolation beyond the data in the startup space. So, the sheer amount of noise makes it hard to find the signal that you’re seeking.

Indeed, some of the “truths” in the startup space are statements that have effectively become accepted as truths through repetition. People repeat these things without really thinking them through.

  • What data support these conclusions?
  • Is the data really good enough or plentiful enough to draw conclusions from, or are we just considering cherry-picked anecdotes?
  • Is that data really even relevant here?
  • What does that data depend on — what are the conditioning variables?
  • What do we have to believe or what has to be true in order for us to believe that conclusion?
  • Is the conclusion a result of extrapolation beyond the actual data?
  • Are these “conclusions” really conclusions, or are they hypotheses and guesses masquerading as conclusions?
  • Are these conclusions still true today?
  • For how long will these conclusions be true?

And so on.

So, if you want a series that says what you expect to hear about startups, turns a stereotype into a full-blown article, or enumerates a top-three list on feeling happy as a founder, then read someone else’s posts.


At this point, you already have a good idea of my writing style. But, I’ll add some flavor to the mix.

Stylistically, my writing is rather direct — I challenge weakly-supported dogma, and I take risks.

For the physics types, I authored papers placing values on absolute scales here and here. Here’s a paper by someone I know, telling the world that I seem to have made a mistake on one of the species that I investigated. I guess that’s what I get for correcting others’ research in some of my other papers…

But it’s for the best, if my value was actually incorrect; we discussed it several years ago, but we never isolated and confirmed a convincing root cause of the difference.

Also, in the spirit of full disclosure, I’ll mention that most of my academic publications appeared in physics journals. I’ve read and learned a lot about copywriting, which has probably helped my style, but I am fundamentally academic in nature.

So, if the tone comes off as a little too academic, then feel free to open a beverage of your choice, or whatever else does it for you, to take the edge off.

Plans For The Series

I really don’t know how many posts will comprise this series. I have a plan, but I already had to split this post into two posts, so…yeah. We’ll see, just hold on tight.

As I mentioned, I plan to cover business and technical aspects within the broader context of the startup journey. I plan to get pretty technical in some posts, but to remain high-level in other posts, depending on the topics and goals of each article. I generally try to make sure that every article that I write has something for everyone, though, so you could read these posts at the level that’s appropriate and helpful or useful to you.

Finally, as I mentioned, expect reasonably well-considered opinions and interpretations. These are data points in my entrepreneurial journey, but they are rooted in subjective experience. These are not truths etched into a stone tablet. Your experiences may not match mine. Your interpretations may not match mine.

And if you are experiencing a burning desire to peruse my own background more deeply for whatever reason before we take this journey together (but don’t get all judgmental on me — keep an open mind), then I’m easily found on Medium, LinkedIn, Quora, AngelList, Facebook, and Twitter.

Anyway, let’s start by covering some background, which is to say, let’s (finally!) explore the topic that forms the title of this blog post.

The Decision To Start A Company

Frankly, this section of the post was harder to start that I thought it would be. It really can go so many different ways, each of which would lead us down a different path to the company’s start.

But the most useful thing that I can tell you is that I felt ready to start the company:

  • from a technical perspective, I was ready — I had been pushing production code for years, and I have a long track record of learning whatever is necessary to overcome technical challenges in many domains
  • psychologically, I was ready — I have a degree in psychology, and I know my mindset and performance in challenging situations, so I feel comfortable making this assertion
  • from a business perspective, I felt reasonably ready — I had an MBA in Finance and Management & Strategy, I’ve worked with VCs and entrepreneurs, as well as in early-stage and growth-stage companies, so I knew a lot of the mechanics, but not all, though, as we’ll come back to
  • from a career perspective, I was ready — most recently, I had joined Origami Logic as the sixth employee, and I was coming up on my four year anniversary there
  • from a family perspective, I was ready — my wife and I had agreed on a time frame and capital investment cap
  • from a product perspective, I felt ready — I have had hundreds (or more) of product and business ideas over the past few decades, so I wasn’t worried about having nothing to do, and I had a specific idea in mind that I wanted to develop into a product
  • from a personal preference perspective, I was ready — I had wanted to start a company for a long time, and it felt like the right time to do it

Knowing that I was ready was a key part of taking the leap and starting the company.

To anyone considering starting a company, I would recommend rating yourself on each of the dimensions that I listed — technical, psychological, business, career, family, product, and personal preference.

Add any more dimensions that are appropriate for you. What challenges do you face? Consider the lack of income for an extended period of time, especially if you attempt to bootstrap, as I did.

Consider telling your friends and family about your progress, or lack thereof, if their opinions matter to you.

Consider working with investors, co-founders, accelerators, service providers, and so on, if you’ve never done so.

Consider doing everything for the company, including the really mundane stuff. Some people are shocked when they leave a corporate job and then have to figure out things like office equipment.

You don’t have to be at the 100% level across the board — I wasn’t. You just need to know what you’ll have to work on, then you can make the decision that’s right for you.

Don’t rush the decision, by any means.

Some people find starting a company stressful. It’s better to be honest with yourself now, than to find yourself on an extended call to your therapist, who has trouble making out your words as you plow through a trough of Ben & Jerry’s ice cream, while sobbing violently in the bathtub and worrying your cat immensely. Not a pretty picture.

So, ask yourself how you’re going to handle things when stuff gets real.

Wait, It Sounds Like You‘re A Solo Founder???

It does. And I am.

But let’s wrap it up here. We’ll continue the journey soon, so I’m going to hit publish.

Posts In This Series

I’ll update these links as I go. It’s not very DRY, but neither are my eyes as I write these posts (just kidding).


Connect with Jason on Medium, LinkedIn, Quora, AngelList, and Twitter.