Note to the reader: this article was written in July of 2019 and was intended to be published in July of 2020.  Since I was too uncomfortable with some of the content even after a year, it’s being published now on June 3, 2021, with a few redactions.  One thing which appears to be potentially inaccurate is that some of the revenue for web design work may be mixed up with revenue for videography work.



State of the Startup: July 2019

I must confess, it feels like a burden to write this year’s “State of the Startup”.  There’s a couple of reasons for that.  A big one is that I’m working on writing a book and am really tired of looking at my word processor, so writing a blog post feels like a distraction from more critical work.  Another big reason is that while I do see progress from year-to-year in how things are going for me entrepreneurially, it feels really defeating to think this is the 4th edition of this annual post and I still don’t quite feel at all satisfied or comfortable with where I’m at.  I’ve developed a lot of skills and traveled to many places and done a lot of cool things with my life, but I feel quite frustrated by all the failures.  I know failure is an inevitable part of taking risks, but damn is it frustrating and isolating.  In particular, I’m feeling like my work in education is a failure right now.

In reminding myself of the purpose of writing this annual blog post, it was to try and craft a real, concrete narration for someone to follow about what entrepreneurship looks like as its happening.  I thought this could be valuable to someone, if I were to become “successful” one day.  So many books are written in retrospect, after a person has succeeded, I thought maybe watching it as it happened seemed more powerful.  Yet this is all based on some inner pressure put on myself to “make it” and “be a success”.

And I feel somewhat tired of chasing that vision, whatever it looks like.  I set a goal last year to focus on enjoying the process instead of fixating on the outcome and I have not succeeded with that.

I feel tired of building websites for people.  I feel tired of marketing websites.  I feel tired of my life being linked to my computer.  I feel tired of working on my own projects which seem to perpetually fail to make an impact.  I’m tired of working so much in isolation.

But I keep going… mainly because I don’t know what else to do with my life.  Obviously I have to do enough work to support myself at least.  But there’s still this drive to do something meaningful… it’s just becoming frustrating to put in so much time and energy and feel like I don’t really make a dent in any of the issues I aim to solve in the world.  I’m not enjoying this.


Web Design and Development

My web development work was steady the last year… more on the marketing and SEO side than on the website building side.  I rarely had to start cold-calling to drum up businesses… but I also wasn’t making much money.  It was basically just enough to get by every month.

I’ve shown graphs the last few years charting things like revenue, costs, hours spent chasing new business, hours spent building websites, etc.  I have those graphs again, but the data is getting a bit confusing and the graphs are losing their meaning.

The problem with the numerical data is that I spent a lot of time in the last year on a video project which I was paid to do, and I mistakenly lumped the money from that project all in with my web design revenue.  So it’s tough to pull apart what money came from doing video work and what came from web design work and then there’s also digital marketing work mixed in there too.  The expenses also don’t do a good job of including travel costs and equipment costs… It basically just focuses on people I paid to do work.


Voices for Choices

One huge success that I need to remind myself about to lift my spirits is the Voices for Choices video series for MindFreedom.  This project was a massive undertaking, especially for someone with limited video experience.  It really reminded me of the value of working with a team rather than doing all the work myself.  It wasn’t necessarily a big money maker by any means, but it did have a budget to accommodate travel to do interviews, hiring an editor and also people to work on music and audio.  As we just started marketing the 13 videos a few weeks ago (they’ll be released one each week) this summer, I truly hope this makes a meaningful impact for people.  It’s the kind of project I would have done for free but would have taken me 5-7 years, so it’s nice to see that having some financial support behind it made it come to life faster and in a far more polished and professional way than I ever could have done myself.

I worked a lot on this project in the fall and spring.  While the time was trackable because I was in front of a computer, things became inconsistently tracked because my partner on the project also used the same computer and we tracked the time spent on it when she was working too.  So that includes a lot of time she worked when I wasn’t necessarily working.  There was also time we were both sitting together working at the same time. There is also a lot of time we forgot to track it because I wasn’t super focused on tracking the time for the project since I wasn’t billing hourly for it.  I’m always good about tracking time for website clients because I bill many of them hourly, but the video project was a flat rate budget so time-keeping was more for our own reference and records and so my tracking skills weakened.  I don’t really track all of that information properly for generating this annual post, I mainly do more detailed records for my own keeping and for evaluating things.


Drop Shipping Dildos

The drop shipping site I worked on ( took a notable dive in terms of sales.  I know the reason for it and its really based around my courage in attaching my name to the site.  I know it would succeed if it actually had a real human on it, but I don’t feel courageous enough to publicly own the fact I run a dildo website.  And I don’t want to lie and have a fake owner on it or do anything deceitful.  So the conversion rates stay low… they were briefly high when we had a lot of fake reviews on there as an experiment.  I feel bad about that experiment, but have to own the fact I did that.



Peer Unschooling Network

PUN has taken a significant dive in traffic and interest.  I didn’t do a great job of nurturing that community, I really tried to let it run itself.  So that’s somewhat dead these days.  It was a bit embarrassing because I had some folks take an interest in my work and was interviewed for a book (Unschooled), a global homeschooling summit (Homeschooling Global Summit), and by the Alliance for Self-Directed Education – yet this work has actually been unsuccessful.  We are running a Create+Connect mentorship program this summer which is really great to connect a small number of teens but doesn’t really have anything to do with PUN.  We basically just promoted it through the mailing list.  It isn’t actually creating a thriving community.  I have some ideas for the fall of doing some online events like Book Clubs, Open mic Night, or Movie Nights… but I get a sense it’s a very small number of people interested.



I spent a lot of time last year doing comedy.  I don’t track the time on this stuff… it’d be hard to do that since time on the road doesn’t really “count”, and time promoting the shows is trackable but the anxiety and rapid spinning thoughts in my head nonstop about the shows are not trackable.  I did track costs with running advertisements, but that doesn’t emphasize the time to create the ads and monitor/track them.  It’s confusing and none of that even has anything to do with time spent writing and performing!  The Time Tracker was really designed just for my web design/development clients so it’s sort of awkward to include on other projects.

I traveled to a handful of cities and promoted my own shows as part of my Summer of Freedom Comedy Tour (which extended into the fall and just became the Freedom Comedy Tour).  Some of that was really stressful and depressing.  Very low turnouts at the early shows.  But I persevered and kept going and learning how to promote shows and get better responses to ads and such.  Plus, the actual performance got better and better as the year went on.  All the shows were free except for the final one, where I just about broke even for costs between renting the venue, advertising the gig, and charging $5 a ticket.  It really required a lot of my focus and attention to do this work, far more than just showing up and telling jokes for an hour.  So it’s tough to pull this off while also doing so many other projects.  Plus all the driving.  It was really ungrounding being in a different city every week, especially while trying to manage promoting shows and also doing my website work.  I either need to get to a point where I have more people interested in seeing me perform that I can charge more money and attract larger audiences.  I could always go the more traditional route of getting booked on other people’s show where they do all the promotion, but this feels pretty aligned with my goals.  If I want to perform on other people’s shows, might as well just do lots of open mics.

I grew a LOT from this experience.  Doing hour-long sets and promoting my own shows was huge.  I can’t claim they all went well… in fact, I’d admit that really the only performances I had were in Gainesville, FL and Northampton, MA.  But I worked out a lot of kinks and saw where the gaps in the show were and what I can work on at open mics to really build this up into a powerful hour.



I did finally get paid for the lawsuit from the events of 2013.  Maybe I’ll write something telling this story in full at some point.  I still haven’t finished building a website to promote health lighting products.  I just don’t have much of a marketing plan for this.  They are expensive, the benefits are hard to quantify financially, and I’m not really sure people are willing to spend the money.  Too many other priorities are taking place.


What the FisX

Speaking of things which haven’t been a priority.  I’m disappointed to say no more progress came here.  I was super excited about this project moving forward but there was a bit of a roadblock with the script.  I realized that now that this has a “story” built into it, the story really needs a second character, and that second character needs to be developed as much as the lead character.  I’m having a tough time coming up with that, and Payce and I did brainstorm a handful of great ideas, but I feel like I’m really struggling because I’ve never written anything for characters other than myself before.  So I can’t imagine a character and an actor/actress playing them.  A bit of a flaw at the moment, but also not a priority because too many other things are going on right now.


Mental Health Activism

I also got involved in this year’s APA Protest.  It was different than last year – we did a “Virtual Protest”.  This was tricky because I had to step out of my comfort zone and offer to be the lead organizer in making something happen.  We didn’t have enough folks in San Francisco for a live protest, but I offered to fly out and film a “Psychiatrists React” video if people were willing to fund the trip.  It was a big stretch for my comfort zone because I had to 1) step out and offer to lead the event, 2) make a video talking directly about my psych hospitalization experience, 3) invite others to submit videos and not know if they actually would, and 4) ask others to financially support the trip.  I could also include the discomfort of actually standing outside the APA Annual Meeting, just me and the anonymous camera person amongst all the psychiatrists.

I noted in reading last year’s State of the Startup that I was feeling upset about criticism publicly on the internet about my speech.  I really need to develop some thick skin if I’m going to be able to handle working in this space moving forward.

It’s tricky because I see there being more work I want to do in this space that I hold back on because of fear.  Just a few days ago I went to the Mad Pride Parade in Vermont and didn’t speak at all at their open mic portion of the event.  I had things to say, but just felt self-conscious as hell from other public criticism I’ve felt.  At the same time, I also presented some work at the Alternatives Conference a couple weeks ago and that was really well-received.  So growth is definitely happening, but it comes gradually and sometimes there’s a couple steps forward and one step backward.  Hard to quantify and measure directly, but its there.


LEAVE SCHOOL: what your teacher can’t tell you

The big project I’m focusing on now is creating an audio book / app titled “LEAVE SCHOOL: What your teacher can’t tell you” about self-directed education and unschooling for teens.  (I referred to this last year as “School Sucks so Start Your Own”)

I really believe in this project though it is a lot more work that I bargained for.  As it becomes more “real”, my standards go up, which means I want it to be more perfect.  I also don’t know if it will be successful, but I have some pie-in-the-sky dreams for it.  Who knows, this may be the big product that allows me to “make it”.  It also feels a little unaligned with my values because I am going to charge money for it even though I want this information to be free.  But by charging money, I could potentially bring in revenue, which could be spent on marketing.  And that feedback loop could be used to put this audio book in front of millions of young people.  This is a project that started several years back.  I wanted to simply take the Teenage Liberation Handbook and convert it to a audiobook app… but it’s not my book or my words so I don’t have control over the content (though  did speak to the author and she was open to it, just had a lot of things going on).  And so I want to have it be my own content so I’ll have control over the process because it’s really not just about the words in the book but also the marketing strategy and app and everything that goes along with getting that content delivered to the end user.   By the time this State of the Startup is posted, that audio book app will be out and we’ll see if it was a success or not.  I do want to emphasize that I think it’s a really clever idea…. Putting it in the app store which kids are accustomed to purchasing from (I don’t picture them buying the actual book on Amazon or the audio book for Audible) – but having a specific app in the store makes it very accessible.  And I learned a lot from promoting my comedy shows to teens through SnapChat and that information can be used to promote the book.  There is a ton of potential…. But only time will tell if reality matches the vision.

Looking forward…. The plan is to get this audio book out in the fall when school is back in session.  I’ll also continue finding ways to promote the Voices for Choices videos.  I don’t know what will come after that.  I suppose if either of these makes a big impact, it could lead to being able to promote comedy shows in a profitable manner.  Though there’s a natural mis-match there because the book and video series aren’t funny at all… but it might match up with people’s curiosity to see some comedy since a lot of the material is about mental health and education.  But personally, I’m not super stoked about traveling right now.  I got burnt out from being on the road all the time and not feeling I have a home or community anywhere.  So right now I just want to stay in one place for a while and try and make friends instead of running around alone trying to chase after something.


I feel like I frequently write these State of the Startup posts and they are not super optimistic.  Reflection can sometimes be painful.  I usually find that writing these is negative but when I read the one from the previous year, I’m uplifted.

Too much of my identity is linked to what I produce.  I need to get away from that.  That doesn’t mean to stop working… but to somehow stop equating my self-worth to what I create.  I am genuinely excited about the potential of this audio book app…. and am excited about how much people are enjoying the Voices for Choices videos that we made.  So this work is making an impact…. Just an immeasurable one and that is tough to grasp.