My Live AMA on ProductHunt (Questions & Answers)

I had a great time answering questions live questions on ProductHunt yesterday and I had a blast engaging with the audience there.

Unfortunately, I had hoped to use their video integration (via Blab) but there was a last-minute technical glitch which forced me to go
“old school” with it and only type my responses.

I didn’t mind this so much since it allowed me to formulate my thoughts a bit more concisely but it also meant a spent a lot of time typing… which hurt my fingers and didn’t allow me to get all the questions answered.

Not a bad thing, just a “thing” I suppose. Here are some of the questions asked and my responses:


For Someone switching careers to tech Now What would be your advice and if you could share your daily reads?

i have changed “careers” myself a handful of times and continue to do so.

The most important thing to remember is that your so-called “career” is much less about the industry or the company and more about how you understand your own abilities and the value that you want to create for others (and as a natural consequence, yourself). You are your career in many ways which means that finding your own unique path is of critical importance.

The next most important thing beyond a philosophical mindshift is meeting great people in the fields and specific industries that you want to dive into. Want to learn about “machine learning” or “cryptocurrency”? It’s time to snuggle up with like-minded people and start learning a shit-ton from them. Here are a few tips on doing this:

– Head to and troll the crap out of it. Goto the ones that are active.
– Hit people up on LinkedIn and Twitter.
– BE HONEST and HUMBLE about where you are. There is no room for ego when you’re learning and trying to start something fresh. This will give you massive returns.
– Hustle the fuck out of it. Remove distractions that are not core to your career objectives. If this means turning of Netflix or saying no to that “Face of Book” for a bit then you should do that.

Stay focused. You can do this.

Hi John, thanks for joining. You mention in your bio that you’re a career-pivot enthusiast. I was curious what guides this? Is this to learn new things and experience new things?

My career is more about the career of “me” than the industry or business or market.

This isn’t an egocentric perspective, mind you, but one that I’ve learned gives me maximum freedom in the choices that I make and the people that I want to work with.

I am infinitely curious. One of my favorite quotes is from Albert Einstein:

> I have no special talent. I am only passionately curious.

I can say that for certain is me… and perhaps many of you as well. Our goal isn’t to stay static or get stagnant, it’s to “kaizen” (continually improve), to grow, to learn. If that requires us to step out in courage to do something different then we need to do just that.

Constructs, such as “time” are not that big of a deal. So what if you were in one company for just a few months… did you grow?

Finally, “moving on” has less to do with time (see above) and physical location and more about your mindset about what it means to move from season to season. The problem is that people see “career” as binary… and its just not.

When you get married, when you start having kids, your concept of career, responsibility, and a ton of other things change. When someone close dies, when you have a life-changing experience…. things change. Your “career” isn’t impervious to these things… it is deeply tied to those things… perhaps even a consequence of those things……

What games do you like to play when you’re not building or investing?

World of Warcraft. I’ve been playing since Vanilla… 11 years, and then the entire Blizzard franchise since the very beginning.

One of my first startups was a dating website for World of Warcraft players… it was my first startup and my first liquidity event (sale)… that’s when I knew there was something about building your own products and working for yourself. That was super-fun.

If you could build your dream team, who would it consist of and what are you building? (Only rule: must be non-fictional and alive)

I’ve written a few times that I’d love to work with @ev … that guy has done some amazing things in the world of digital publishing and I can’t seem to not stop thinking about it. Learning from him and being mentored and/or coached by him and HIS “dream team” would be amaze.

What are some of the ways you have learned to cope with depression, and who/what has helped to make a difference for you?

My family and my incredible medical providers and/or specialists.

BUT… one of the most important things have been my diet and overall health… when I had my major medical crisis i sought help from the best and then I did something about it. I lost 30 pounds… eating better (“right”) and reworked my entire physical habits. I started doing standing desk 100% of the time and worked out consistently. I cut out the bad food and replaced it with good (or portion controlled).

There’s an intimate relationship between your mind and body… if you’re not physically well… then how do you think you’re mind is doing?

Hi, John. What suggestions would you make to teens looking to get into gaming or tech? What skills would you like them to learn besides coding?

that’s easy: Communication.

If i were to have spent more time in my youth it would have been to focus on the fine art and science of communicating. This is EVERYTHING in our world, both oral and written and everything in-between now.

Most of us pick up on these skills as a consequence of living… but very few of us actually and intentionally invest in our communication skillsets… i would have gone A LOT farther in my career A LOT SOONER if I had learned to be a better communicator…………….

Hi @saddington, thanks for blogging your thoughts over the past years. It’s apparent that you care deeply for the well-being of your teammates. Who are the people you look up to that foster a work culture that values people, instead of mere performance?

There are a bunch of people that are doing great things in the peopleOps space and HR in general… and there are too many to name that are doing really good work.

I think the most important thing to remember when building a functionally-healthy work environment is that it starts with you. You have to believe, at a fundamental level, that this high-bar can actually be achieved. There are a lot of people who give this a ton of lip-service… and even have it part of their “core values” but they don’t actually practice it. Trust me, I’ve been part of those organizations……………….

When you take care of your people you take care of your business. This is core and absolute. It starts with you and sometimes you have to move-on to other places that care about it because the leadership doesn’t.

And that brings me to my next point… if leadership isn’t on board with this type of thinking then they probably never will. And, you know it when you see it. Bad leadership is rampant in silicon valley. It gets overlooked based on hype, “profitability”, and capital raising. But, it always catches up.

Hi @saddington. I’m Japanese engineer. So why do you use .tokyo domain and what kinda hardware do you use?

I thought it would be fun! There wasn’t any special science behind it or any special thinking… TBH.

Hardware? I have a list here:

Thanks for being here today. 🙌During your career to date, what has been your a) most challenging moment and how did you overcome it? b) proudest moment and why? c) most surprising moment?

i feel like I encounter challenges every single day that rob me of precious sleep!

The biggest challenge of any entrepreneur, solo or if you run a company, can be loneliness and the mental and emotional taxation that comes with building anything creative. I am a suicide survivor ( ) and know what it’s like first-hand to deal with this mental disorder daily. It takes courage and perseverance to stick it out some days…

My proudest moment has been my most important startup: My family, and my wife in particular, sticking together for the last 10+ years together as I have gone in and out of employment, building projects, companies, raising money, losing a ton of it, and moving 17 times in the last decade… they are everything to me! They are my foundation… and if you dont’ have somethign like that…. well, good luck………

My most surprising moment(s) have come when I’ve learned more about myself than about my business or anything else like that. Learning about my diagnosis of being a high-functioning autistic adult was huge. Stuff like that.

being as prolific a blogger as you are– what are some tips you would give on becoming a more consistent and disciplined blogger?

It’s all about discipline:

And it’s not about any formula or “system”……….. it’s almost too simple for most people to admit:

– Get up in the morning
– brush teeth, eat some food
– look at schedule
– is writing in your schedule?
– if no, put it in the calendar.
– if yes, wait until it’s time…


What is one of the greatest adventures you’ve had, and what prompted it?

I went on a trip to bosnia, sarajevo. I free-climbed a mountain in split, croatia, and almost died. I feel and split my left leg open from the ankle to the hip, and have the big scar to prove it.

it cut so deep and sliced my leg so perfectly that i didnt’ bleed for a while (eventually it did). it cut all nerves in my lower leg and i was able to make it back to the basecamp, almost… a friend luckily was coming up and saved my life. i got a huge tattoo over it.

Hi @saddington thanks so much for joining us today. Would love to hear if were to start the process of learning to code again, how you would you do it? What language would you learn? What resources would you use? Love your advice.

learning to code is simple… and very hard… but the fundamentals are still the same: stay humble, work hard, and find DEDICATED time to do it.

Even if you know code and have been doing it for a while, there’s no room for EGO either. I wrote this a while back:

So, even if you know code its still worth to start from the bottom and go from there.

Finally, find a mentor or a coach… do apprentice-style learning and get a TON of help!

How do you choose your next project? Does passion come organically, or do you have a process?

There isn’t an obvious process, but the most important “technique” that I’ve used in the past lands in two major buckets:

1) Long-standing interests and curiosities.

For instance, my passion for digital communication technologies, like online publishing, has created a ton of projects (and businesses!) over the years. I seem to come back to these things year over year and building them feels natural and exciting every single time.

If you find yourself to continuing to come back to the same types of industries or interests…. then there’s a good chance that there’s something there for you in terms of a project or even a larger business.

2) Personal relationships (and conversations).

The best “ideas” that i’ve ever had are ones that have been massaged through by people that i trust and respect, people that I love to bounce ideas off of. My idea starts half-baked… and doesn’t really take real form until I talk with people about it. This is most noticeable with my wife who cuts right to the quick about my ideas and lets me know the hard truth about things.

Great partners (business) will also do this. Start companies and projects with those types of people, honest, forthcoming people, who love you and want to work with you because they know you, not because they want to get something out of you.

since you’ve built a WordPress product in the past, if you were to develop a new WordPress plugin today, where would your marketing efforts be spent?

I’d honestly stay away from it. When things get super-popular I (and maybe this is just me) I start looking elsewhere. It’s time to do something new.

What is one of one your favorite projects to date (even something you did as a kid)?

I built a tiny store to sell Ninja Stars to my classmates. I built them in origami and sold them for a quarter. I realized (supply & demand) that I could up my sales if I increased the price. This was in second grade and it was life-changing for a number of reasons:

1. You can build things that you love.
2. People can also love the things you build MORE than you.
3. You can actually make money building things that you love and that people love more than you.
4. Utility == fun…. those ninja stars didn’t change the world but they were hella fun…. and THAT was the utility (e.g. value).
5. You can rinse and repeat this model to infinity.

that’s how i see the world.

Welcome, John! How do you decide which new products to build?

1. Build products that you want for yourself.

This is one of the most important things. If you don’t learn to “scratch your own itch” then you won’t ever be solving a problem that YOU, YOURSELF, understand. So many entrepreneurs stick their noses into industries, markets, and other such “niches” that they haven’t ever fundamentally encountered or had issue with.

Build products that solve the problems that you have and you’ll always find a market.

2. Build products that are built around your core interests (i.e. you)

You know yourself better than really anything else… then why do so many entrepreneurs build OTHER entrepreneur’s dreams? Build your own.

3. What makes you curious?

I’m consistently curious about only a select few things… and I keep going back to these things all the time. Those things are the closest to me and the things that I really want to learn more about. There’s a good chance that by attacking these things I will find greater success because of my deep-level interest and curiosity in them.

And don’t lie to yourself… you and I are so easily self-deceived into “liking” a ton of shit. No… we are only TRULY curious about a select few things……..

maybe a dumb question, but why’d you ditch your old Twitter account? Seems like you’d want to hold on to all those followers!

This isn’t a terrible question and one i’ve answered here:

In essence, I’ve gone through many seasons where I just wanted to “reset”… i think we’ve all experienced things like this, where we want to just start over, start fresh… and i think more of us have to start thinking about this online and in the digital context.

We are ever-evolving people but we are building “static” monoliths of never-changing personal brands… that just doesn’t seem right, does it?

As a seasoned developer, what do you think is most inhibiting younger folks of all backgrounds from becoming developers at a younger age? Do you think development should be part of the core curriculum (in the US) like english, math, etc.?

I’m not sure everyone should be a developer professionally but I think everyone should be “literate”.

What I mean by that is the same for any liberal arts that are taught. We should all be “literate” in basic concepts of math, the sciences, and computer programming and engineering. But not everyone needs to go the distance with either one of those…

Those that want to learn and become developers will do so… but we, as educators (and parents/coaches/mentors/facilitators) have to provide:

– Access
– Awareness
– Education
– Resources

… To make it all possible. As a parent (i’ve got a 9 and a 5 year old girl) that’s my goal: Make things available for them in a great way to encounter them and to see if they like it. If they don’t, we move on. If they do, we dive deeper.

It’s organic, but it feels much better and much more natural.

What is the latest industry or experience to trigger your curiosity?

right now, i’m super-fascinated about team-building and leadership / management.

you would think that i’d be half-way decent at it since i’ve started a few co’s… but honestly i think i’ve lucked most of my way there… and there’s a difference between being okay at it and having a fast-growing company and actually being great at it, especially in a company that’s not in hyper-growth.

Hyper-growth can cover a multitude of sins… and that’s a bad thing (obviously).

So, what I want to do is really spend more time now on learning how to be an amazing manager, mentor, leader, and coach. That aligns with a ton of my experience and passions and previous interests…. but more importantly, I WANT to learn those things.

EdTech is one of the industries that falls naturally in line with those things… and people in that industry are looking very closely at how to build those things as a fundamental level… in ways that we’ve never really considered.

how do you plan on going about learning more / improving your leadership/mgmt skills?

Great question… getting coached and mentored is a huge part of it. Finding great companies to work with and/or for is also part of it. Starting a “new co” is always an option as well… but I have to ask my wife about that.

Practicing this is the most important thing though… so whatever context I find myself in I have to intentionally practice it to get better… just reading / studying it is nonsense and pretty

What has been your best purchase for less than $100? What about over $100?

Great question. I’ve made a ton of purchases over the years but the one that’s been the best is my many notebooks that I’ve used to capture ideas. Those have been fantastic and I’ve got a list of them that I use here:

Over $100? Hmm, tons of those as well, but clearly I love the devices I use and I list out few on my Colophon:

But, I really love my Bose Noise Canceling headphones… they are the very, very best! —>

Hey what is one product you wish you had built?

I don’t have any regrets and my time (like yours) is so limited… so there aren’t any projects that I wish that I’ve built or that I feel like I’ve missed out on…

I’m always looking forward to the next thing… which can be a blessing and curse. But now I’ve learned that looking forward without the RIGHT people around you is a terrible way of doing projects or building a company. It’s the people that matter more than anything else in the world.

What types of apps or individuals do you look for to invest in? What investment space do you find most compelling right now?

Great question…….. and one I’m not sure I’ve very good at answering.

The problem that I see (and a common trap) is to believe that just because are half-way decent at being on “one side of the table” (i.e. entrepreneur who’s raised venture capital) that you’d be just as good on the other side (i.e. venture capitalist investing in entrepreneurs).

I’ve done okay on one side… but I’m not arrogant (or foolish) enough to blindly believe that I”m good at picking out the winners as a natural consequence…

As such, i’ve limited my own investing and am not entirely sure I’d be very good as a full-time VC… perhaps I’d suck. who’s to know…?

in as many organizations that you’ve been a part of– what’s the most sure-fire way to spot an unhealthy and/or deteriorating culture?

you know it when you see / sense / feel it. you KNOW when it’s not healthy… but you justify or rationalize it away for a ton of different reasons. Most people are just not brave enough to say anything when they see it or they are too afraid of their own jobs to raise their hand and say “hey, there’s something wrong here…”

We know more about the health of our organizations than we allow or admit ourselves to believe… if you head to the office feeling afraid, anxious, or anything else even remotely close to that… then something’s wrong. It could be the org, it could be you.. it’s probably a bit of both.

Honest conversations is where it starts. Building an organization based on Trust and not Fear is so important:

Healthy organizations are built on that.