1. Treating employees like friends

In the early days I tried to be the Buddy-Goodtime-Boss. I would treat employees like friends by talking a lot about their emotions, friending them up on Twitter and Facebook, going drinking with them after work, etc.

The problem is that I needed to be objective about their performance and sometimes ask them to move on to another job.

I found that it was almost impossible to switch from friend to objective, business owner. It’s confusing and unfair to employees to make it appear that you’re friends and then have to potentially fire them for performance issues.

Currently, I treat my employees with respect and kindness but make it clear that we have a professional relationship. Both of us have to hold up our side of the bargain and hit our targets, or tough decisions will have to be made.

Ben Horowitz wrote a great post on this issue which I’d recommend reading.

2. Not keeping track of delegated tasks

I undermined my own authority by asking employees to do a task by a certain date, and then not following up with them when it was due. The unofficial message was that I wasn’t really serious when I set a deadline.

I now keep track of every task I delegate by using Trello. I’ve got a board called ‘Delegated’ and each person has their own list. Every time I ask someone to complete a task, I create a new card and add it to their list. I’ll write a few notes and occasionally add a checklist to the card.

When I do my weekly 1-on-1 meetings with my Leadership Team (those who report to me directly) I go through their list and ask for updates on every card.

3. Not understanding our P&L and Balance Sheet

I met with our accountant quarterly to sign off the accounts and it always felt like a nuisance. I thought all that mattered was the cash-flow. The problem is that the P&L, Balance Sheet and Cash-Flow were all working together to give me a complete picture of the business. However, I was just focusing on how much cash we had and whether we had enough to make it through the next three months.

When it came time to sell my events business, it turned out our Balance Sheet was in bad shape because we had collected a lot of revenue that we couldn’t recognize because it was for a future event. That means it was a liability, not an asset. Ouch.

That mistake cost me around $175,000 personally as the buyer knocked that amount off the purchase price. When someone buys your company, the transaction is done on a ‘zero balance sheet’ meaning they pay extra for assets or take away cash for liabilities.

This was a timing issue and if I had understood it, I could’ve timed the sale of the business more effectively to maximize the purchase price.

A Little Story for You ...

Like all startup founders, I'm working on generating organic traffic for Maple so I can reduce my ad budget and drop my CAC.

I came across a post by @jakezward and @MackGrenfell showcasing their AI content writer byword.ai. The numbers are very compelling.

Essentially, if a business wants to generate significant organic search traffic, they can now use byword.ai to write high quality blog articles, at scale, for ~$3.70 per article.

This is obviously a shocking reduction in the traditional costs of creating high-quality written content:

Even if we assume the bottom-end on traditional costs of $145, byword is 39x cheaper 🤯

AND it can write a 1,000 articles in minutes (and it has extra cool features like research reports and interlinking articles).

What does Google Say About All of This?

Google's official stance on AI-generated content is essentially "We rank good content. Good content is good content, regardless of if it's created by humans or machines." Read more here on byword's blog.

Let's go!

So I was sold. The next morning, I was planning to get out my debit card, sign up for byword and try generating 80 articles for $299.

But Wait ... Can't I Just Build it Myself?

When I woke up the next day I thought "Wait a minute, why don't I just build my own and save a ton of money?"

So I spent a couple hours and put together a simple version in Python and was pretty happy with the results.

Shockingly, the API costs were only $0.1192 per article.

I refined and improved the script over the next couple days and now it's cranking out hundreds of high quality articles daily for me. I just started this week so I can't measure the impact yet, but based on Jake and Mack's research, I'm optimistic.

It doesn't have all the functionality of byword.ai but it's enough for me.

If you don't know how to code or don't have time, byword is an amazing solution and is worth every penny.

But if you can run a Python script and don't need the extra features, my script is ~31x cheaper than Byword, and 1,216x cheaper than traditional content creation costs.

Say Hello to Article Writer

I know ... amazing name right? 😂

I thought "What would a bootstrapped founder, like me, pay to save a couple days of messing around to get this working?" and $99 seemed right.

So here it is. You can own the code for $99.

Here's How it Works

1. Purchase the code.
2. I add you as a collaborator to the GitHub repo. If you don't have a GitHub account, just shoot me an email at ryan@ryancarson.com.
3. Git clone the repo and update the configuration variables in app.py.
4. Research and build a list of articles you'd like to create and add them to topics.csv.
5. Add your OpenAI API Key.
6. python app.py and take a quick nap.
7. Upload the files and images to your blog.
8. Wait and measure the organic traffic impact.

If you're not 100% happy, you can request a refund within 7 days of your purchase. Reach out by email at ryan@ryancarson.com.

It was a bold move and one that not everyone was convinced of. We proposed to change the way the company operated and give all employees 100% control of their time and let them decide what they work on each day. From now on no one would tell anyone what to do, not even the CEO. (Me!)

This is not a new idea. Valve, GitHub, Gore Associates and Medium (and probably more) are all #NoManager companies. Knowing that someone has done it before us didn’t make it any less daunting or even any easier. This is the story of how we did it, why we did it, the highs the lows and a few pointers for anyone thinking this craziness might be for them.

Why we Removed our Managers

We started the company in 2010 and operated in the normal command-and-control structure. By 2013 we had grown to 60 people with seven managers and four executives. As we added more people to the team, we noticed something disconcerting: rumors, politics and complaints started appearing.

Alan, my Co-Founder, and I started exploring possible solutions and considered removing the lowest layer of managers and asking them to go back into producing (which is what they were originally hired for). Then we went up the chain and asked hard questions about the value of the mid-tier managers, and then we kept going all the way to the executives at the top.

What if we removed all management and simply empowered everyone to choose what they do every day? We laughed at first and then the conversation turned serious. We had hired talented and motivated people. Did they need managers?

I can only speak from experience so I’ll limit this to my journey being an employee at two companies and running four companies.

In my experience, managers started off as workers and then moved up the ladder, getting farther and farther from the front line. They gained power but slowly lost their touch with the day-to-day realities of talking to customers and actually creating solutions to their problems. The manager’s team lost respect for them because they could no longer produce, which means they would set unrealistic deadlines.

Everyone was getting abstracted away from actually doing and instead focused all their attention on structuring.

As our team grew, we spent more and more time talking about priorities, aligning everyone and checking in on progress. The whole structure we designed was taking power and responsibility away from everyone on the front lines.

What do Managers Do?

In my experience, managers’ responsibilities were …

1. Communicating messages from top to bottom
2. Settling disputes
3. Managing careers
4. Keeping their teams motivated and happy
5. Shielding their teams from things they didn’t think they needed to know

If we could find a way to replace the function of the managers and focus everyone on actually producing for our Students (customers) then it would actually be possible to be a #NoManager company. In my future posts I’ll explain how we’re doing this at Treehouse.

What Motivates People?

In my experience, people want to be amazing at their job. I can’t count the number of times that people had really great ideas but were powerless to implement them. I watched as they went from zealous excitement to indifferent cynicism.

If you have 10 minutes, please watch this video by Dan Pink: Drive: The surprising truth about what motivates us. I think it sums up almost all my thoughts on why we decided to remove management.

Good managers act like servants to their team but far too many like the power and let it go to their heads. If Treehouse ever grows to 500 people, we’d need at least 50 managers. If we were starting to have morale problems now, what would that be like? Blurgh.

Go time!

Alan and I decided that if we were going to do this, the company would have to enact it by a majority vote.

The Treehouse Team is spread over the entire United States (with one person in the UK) so we do most of our communication in an internal forum called Convoy. We wrote an epic post on Convoy called Radical new idea: No managers at Treehouse, took a deep breath and hit the post button. The whole company ground to a halt for two days as 447 comments were posted, upvotes and downvotes were cast and passionate opinions flared.

After two days, we did a company-wide Q&A over video and at the end we asked everyone to vote via an online form. The votes flooded in and over 90% voted to go flat.

It was go time. Now the real work would begin.

How We Transitioned to No Managers

Once 90% of the company voted to remove management, we started the task of transitioning the company to the new flat structure. The first thing we did was write a huge FAQ for everyone. We did this in Google Docs so people could comment directly in the doc and everyone could see their questions and our following answers. I’ll cover the FAQ content below.

Once the FAQ had been written, Mike Watson created a detailed list of logistical things that needed to happen in order to transition successfully. Example: Who would be doing the backups of our video?

Here’s a simplified version of our FAQ. It will answer many of your questions about how we operate as a #NoManager company.

Projects

Projects are the primary unit of work at Treehouse. Anyone can have an idea and propose a Project. Projects do not have to relate to the core expertise you were hired for. Example: A Designer could propose a project to teach a course.

How do Projects work?

If you have an idea …

1. Open up Flow (our internal tool).
2. Click ‘Propose a Project’.
3. Explain the Project goals.
4. Determine how you will measure success. We encourage you to use measurable statistics and metrics.
5. Choose a Focus Area (Education, Marketing, Finance, etc)
6. Add the Team roles that are necessary to complete the Project (Developer, Designer, Audio, Video, Data Scientist, etc)
7. Spread the word and try to recruit great people to your Project. A good idea is to create a post in Convoy (our internal forum) and ping people on HipChat (our company-wide chat tool).
8. People join your Project by going to the Project pitch and clicking 'Join’.
9. Once enough people join, hit 'Start’. If you don’t need anyone else to help, you can just begin, providing you’ve bounced the idea off people who need to know and starting the new Project will not hamper your ability to execute on existing Project commitments.
10. If you don’t gain enough support for your Project you can click 'Abandon’.

Once your Project starts …

1. Conduct an initial kickoff meeting with the new Project team
2. Once a day, everyone working on the Project needs to post a quick update on where they’re at with the Project and what % complete they are with their tasks. For example, if you’re the Designer, and you feel like you’re 50% done and the Developer feels they’re currently 0% done, assuming it is a two person team the average ‘completeness’ will average out at 25%. The average completeness for each Project will be posted publicly to give the whole company an idea of how complete each Project is.

After your Project completes …

1. The team measures how successful the Project was and posts a post-mortem thread on the Project in Convoy (our internal forum).
2. The Project team is responsible for providing ongoing support and maintenance of that Project

Can I leave a Project before it completes?

If you want to move to a new Project, you chat to your current Project Team to let them know you’ll be moving on and then simply sign up for another Project. It’s not cool to leave your team hanging when they need you, and we would expect that poorly timed and communicated moves from teams would be reflected in your peer reviews.

How big can a Project team be?

This is naturally dependent on the nature of the Project. That said, it is in everyone’s best interest to keep the size of Project teams to a minimum. Remember our biggest costs at Treehouse are team salary and the opportunity cost of your time.

How many Projects can I work on at once?

It’s up to you, just don’t disappoint any of the Teams you’ve joined by getting behind schedule and dragging down the team. The importance of focus in creating quality cannot be understated.

Many of the folks at GitHub have blogged about how this is one of their biggest day-to-day challenges: over-committing. Better to over-deliver than under perform.

What happens if a team forms, and produces a Project that they all thought was a good idea. But when it’s complete, it turns out to be of poor quality. Who decides if it goes live or not?

We cannot make a rule for this that will always work. There needs to be a robust QA structure in place but beyond that we’re relying on everyone’s good judgement to decide if something is shippable. Once it ships we need the Project Team to be measuring its success and reporting back on whether it succeeded or failed.

If I propose a Project, but there’s not enough bandwidth, do I wait on Team Members to finish other Projects or convince others to join mine instead, or do I just have to join another member’s Project in the meantime?

There will be a very small percentage of Project Proposals that actually get started. If yours doesn’t gain traction right away, then just jump into another Project or find something you can do on your own that uses your skills to best serve our Students and advance our Mission.

Where do I post my daily Project updates?

For each Project you’re working on, you need to do a daily update in Flow and include your % completeness.

It is vital that everyone posts daily updates on what they’re working on or this whole idea will fall down.

Will people ‘lead’ Projects?

Each Project Team will have it’s own way of working. Sometimes the best thing to do will be to elect a leader who makes sure everything is driving forward and organized, for example coordinating with teams outside of that particular Project or product. Other times, it may make sense to not have a leader and just divide roles and tasks as needed.

Some people are natural leaders and will automatically influence Projects because of their experience and charisma. However, no one is forced to follow anyone so only people how are actually good at leading will be 'leaders’. As the saying goes, “If you call a meeting an no one shows up, then you’re not a leader.”

How does everyone know what’s happening on other Projects?

You go to the Project page in Flow and read the status updates. If you need more info you can jump into HipChat (company-wide chat room). We discourage email as it creates information silos.

What tools do Project Teams use? (Trello, Asana, etc)?

After a Project has been started, it’s up to the Project Team to use whatever tool is best suited for their work.

Who prioritizes Projects?

There isn’t any top-down prioritization (unless we are required by law to act on an issue or some “red alert” type work is required, which should be rare). Each person will be prioritizing their todos based on maximizing their ability to advance the company-wide goals and Mission.

How do we spend money and are there budgets?

We want to be clear about something, moving to a flat structure does not mean everyone has carte blanche with Treehouse financial resources. There is one exception:

We are going to start off with no set budgets for Projects at Treehouse. If your team needs to spend less than $500, then you can go ahead and do it on the condition that everyone on the Project Team has unanimously approved it. This will probably mean that whenever you spend money, you have to file a claim through Expensify or you can request a cash allowance from the company. Project teams can spend up to $500 if unanimously agreed amongst the team.

If a Project’s spend increases or is expected to increase above $500 in aggregate, you need the approval of the Co-Founders.

Project spending will be listed publicly so we can all see who’s spending what. Remember, it is absolutely important that we exercise as much thriftiness as possible. When the company has more financials resources (is comfortably generating positive free cash flow) we will probably increase the thresholds for approval above.

Again, for any spending not related to Projects, for example travel, product based spending, non-Project related supplies, etc., you will need to get approval from the CFO.

What’s happening with our current top five priorities?

They have been deprecated. You all will be deciding your day-to-day priorities. The Co-Founders will be communicating their 50,000-foot view of the monthly priorities but they are just guides.

How do we make decisions?

We use our company wide goals, Mission Statement, and impact on free cash flow as a guide for decision making.

Who decides company-wide priorities? Who sets the general direction for the company?

Alan and Ryan (the Co-Founders) are actively steering the ship and setting company-wide goals, our Mission Statement and areas of focus.

What are the Co-Founder’s roles in this new system?

Ryan and Alan are still very much leaders of the company. They will decide on company-wide goals, make sure our Mission remains relevant driving force, and keep our current areas of focus updated.

No Ladder to Climb

Now that we’ve removed managers, there isn’t a traditional career ladder to climb. At most companies the way to get more money and influence is by becoming a manager. How does this work in a #NoManagers company?

Everyone is hired at Treehouse at an industry-standard salary level that matches their job description. Most of our team is distributed and outside of expensive outlier markets (like Silicon Valley or NYC).

The only way to get a salary increase is by performing consistently well in reviews. We don’t have a profit-sharing plan or bonuses (other than the sales team which has a traditional sales team bonus structure).

One of the great advantages of a #NoManager company is that people aren’t forced to go into management to get more money or increase their power. Instead of climbing the corporate ladder they can focus on getting better and better at what they love and were hired to do.

Peer Reviews

Accountability is vital for #NoManager companies to succeed. Since no one is telling anyone what to do, slackers could just sit around and do nothing, right? Peer Reviews make sure that bad folks are rooted out and asked to leave the company. We chose to implement a system that’s similar to the 360 Degree Review but with a twist. I’ll explain how it works below.

How Reviews Work: The Review Cycle

A Review Cycle will occur every three months. Each person writes anonymous reviews of colleagues that they’ve worked with closely since the last review period*. For example, if you were a Developer and you worked with a Designer and a Customer Support person on a Project, you’d review both of them and they’d both review you.

What does “worked with closely” mean? Typically this would include anyone you worked with on a Project or product since the last reviews occurred. It will also include people you collaborate with closely even if you aren’t explicitly involved on a Project with them - for example, Designers are going to be in constant communication and will collaborate with each other on ideas even if they’re not officially on Projects with each other, and we want to be sure to capture that interaction in our review process. If a Project is extremely quick (for example, less than a day) then a review isn’t needed.

The great thing about only reviewing people that you actually worked with, is that you know if they were any good at their job. You experience it first hand, instead of through a manager’s report or through occasional interaction.

Everyone is expected to write a solid review in ~15-20 mins, per person. It could take much less time if we’re organized about keeping notes between review cycles.

Reviews are submitted to a Review Committee made up of myself, Alan (my Co-Founder), Mike (CFO) and Rich (Accounts). The Review Committee then reviews all submissions and asks for clarification if needed. Afterwards, they anonymize and consolidate all reviews on an individual into one Review Document. That document will be used to guide the review (in-person or Google Hangout between person being reviewed and the review committee). Each person gets a copy of their review documents.

The Review Questions

You rate your colleague on the review form (we use a password protected form on Wufoo) on the following things:

1. Objective judgement
2. Communication
3. Energy giver, positive working style, attitude and effort
4. Level of skill

You have to choose between 1 - 5 for each area and can add accompanying text to explain your answer.

1. Outstanding
2. Exceeds expectations
3. Meets expectations
4. Below expectations
5. Unsatisfactory
6. Not applicable

We also have an optional text field for additional comments and/or constructive criticism for the person you’re reviewing.

We also ask everyone to answer the following questions about themselves:

1. How do you think you are doing?
2. How do you think Treehouse is doing?
3. How do you think your team is doing?
4. What’s keeping you from doing the best work of your life?
5. Is there anything else you think the Review Committee should be aware of?

Good vs Bad Reviews

If someone performs below expectations they will most likely not be recommended for a raise. Depending on the circumstances for why they performed below expectations, they may be issued with a formal warning to improve performance. If subsequent reviews are below expectations again and performance hasn’t improved, they will probably be asked to leave Treehouse.

Major Cons

Two large drawbacks to this Peer Review system so far are:

1. It is very time consuming. As we grow the company we’ll need to find a way to make this as seamless and easy as possible. Theoretically it should scale as there’s a practical limit to the number of people you can work closely with during a 3-month period - no matter how large the company grows.
2. People weren’t as harsh on each other as they should’ve been. Our belief is that because we only finished the first review cycle that people are just getting used the the system. In the future however, feedback will need to be much more constructively critical to be valuable.

Raises

Alan and I are in control of raises. Recommendations from the Review Committee and Treehouse’s financial situation will be the key determining drivers of whether or not a raise will be given. As of now, there are two types of raises that can be awarded at Treehouse:

1. Good Performance Increase

The key input to determining performance is the peer review process. The review committee will look at all the feedback compiled, and contextualize each individual performance within the company. People who perform well will be awarded with increases to their salary. We may also take into account other factors, for example student feedback. The Review Committee has established basic salary bands for each job role and when a salary increase is awarded, the person goes up to the next level. There is an eventual ceiling to the salary level for a job role. If someone wants more money once they’ve hit the ceiling, then they either have to change jobs to a more lucrative position (but they’ll have to apply for the job like normal candidates) or leave the company.

2. Cost of Living Increase

Everyone who is performing well will receive a cost of living increase for their hard work. In Q1 of each calendar year, everyone that is performing at or above expectations will be awarded with an increase in their annual salary. This increase will most likely be based on inflation, but will also take into account market rates and conditions.

Confidentiality

It’s important to keep reviews confidential. This encourages more direct feedback. People shouldn’t share the content of their reviews with anyone other than the Review Committee. Sharing reviews with anyone outside this group will mean you’ll get an automatic official warning, and possibly be asked to leave Treehouse immediately.

Communication Tools

We actively discourage use of email because it silos information, discourages accountability and causes busywork. The default mode of communication at Treehouse is ‘public’. This is important because without managers, everyone needs to be able to drop into a Project and understand where it’s at. If all the progress and information is hidden away in email, no one can access it except the sender and receiver.

We have four primary tools:

1. Convoy - General discussions, celebrations, animated GIFs, banter and trolling
2. Flow - Project status
3. ipChat - Group chat and IM
4. Email and Docs - Google Apps

Our hope is to open source Convoy and Flow at some point, but it’s not high on our priority list right now.

Convoy

We’ve found that the forum model works really well for company-wide discussions. We built a simple Reddit-clone to do this (read more on that here) called Convoy.

Email is a terrible tool for group discussion because …

1. It clutters everyone’s inbox
2. It’s hard to parse discussions because of the lack of threading
3. You have to evaluate if you should open/archive/delete/star each incoming email

Convoy is great for company-wide discussions because …

1. You only read/interact with things that interest you
2. Voting up/down adds a subtle and quick way to interact with other people without having to type
3. We have person-tagging so that if you want someone to see something, you simply type @persons-name and they get a notification inside Convoy (not email).

Convoy has worked wonderfully for us. We use it for …

1. Discussing competitors
2. Throwing around ideas
3. Trolling each other and having fun
4. Celebrating victories
5. Discussing industry news or trends

The drawback of Convoy is that it can be distracting. You need to have a highly disciplined team to self-police themselves. This is a general drawback of #NoManagers - it’s noisier and more chaotic. Our belief, however, is that creativity and innovation arise from the chaos.

Flow

Since we don’t have Managers to decide which ideas get implemented, we had to build a simple tool to allow anyone to propose ideas and tell the whole Team.

I explained how we use Flow in this post, so if you want details, please head there.

Once a Project is started, there is a discussion forum attached to the Flow project. If you want to discuss something then you create a new discussion thread. Everyone who’s joined the Project is then emailed so they can stay in the loop. We felt email was necessary because if you’ve joined a Project, then you should be aware of all discussions related to the Project.

Every day, you update your status on the Project in Flow. This way anyone can drop by the Project page and see what’s happening, without bothering anyone.

The actually project management happens outside Flow. Each Project chooses whatever software or system they feel is best suited for the Project. This has caused some friction in the company as some people want Flow to also offer Project Management functionality (like Basecamp or Trello). I’ve been against this idea as I feel it could bloat pretty quickly into a Trello/Basecamp clone, which is overkill.

Flow is basically a simple communication tool: Which Projects are happening, who is working on them and what their current status is.

HipChat

We use a group-chat/IM tool called HipChat. It’s a desktop/mobile/web app for private group chat. We currently have 23 rooms spanning everything from 'Design’, 'Marketing’, 'Audio’ to 'The Nerd Herd’.

Anyone can create a room and they’re primarily used for quick-fire chat related to Projects. Because I’m the CEO, I join almost all rooms so I can get a birds-eye view of what’s happening.

We ask everyone in the company to log into HipChat during work hours. We’re spread out over the World so everyone needs to be contactable.

Email and Docs

We use Google Apps for our email and documents. We use commenting and live-editing in Google Docs quite a bit. We only use Excel for finances (Google Spreadsheets can’t handle the complex spreadsheets we need for financial models).

Email is email. Blech. Here are the email rules …

1. Don’t use it unless it’s your last resort
2. Never discuss Projects in email. Use the discussion forum in the Flow Project. All information should be as public as possible.
3. Don’t worry about inbox zero. Focus on your Projects in Flow. Ideally check your email only once or twice a day.

Urgency

We use this rubric to determine the urgency of communication …

• Phone or Google Hangout: Need an answer immediately
• IM or Text: Need an answer in the next hour
• Flow Discussion: Need an answer in next day or two
• Email: Need an answer in next day or two
• Convoy: No answer required

The concept of a one-person startup, once a rare and challenging endeavor, is rapidly emerging as a feasible and increasingly popular business model. This shift is powered by advancements in technology, particularly in the realm of artificial intelligence and digital platforms. The story of Maple, an AI personal sales coach that I developed single-handedly, stands as a testament to this new era of solo entrepreneurship.

In this blog post, we'll explore how the traditional startup model is evolving. Gone are the days when launching a tech company necessitated a founder to team up with a CTO, raise substantial venture capital, and build a large team. Instead, we're entering an era where solo founders, with the aid of cutting-edge technology, can single-handedly steer their startups towards success.

The Traditional Startup Model

Traditionally, launching a startup involved assembling a team of co-founders, each bringing specific expertise in technology, marketing, or business development. This process often required extensive networking, significant time investment, and the challenging task of aligning visions and goals. Additionally, startups typically sought external funding, leading to a complex dance of pitching to investors and, often, sacrificing equity and control in return for capital.

This model also placed immense pressure on startups to prioritize rapid growth over profitability, sometimes leading to unsustainable business practices. The focus was on scaling quickly to satisfy investors' expectations, which often meant aggressive hiring, rapid expansion, and a relentless pursuit of market share, sometimes at the expense of long-term stability and founder vision.

The Emerging Solo Founder Model

The solo founder model flips the traditional startup script. Enabled by AI and modern technology, individual entrepreneurs can now perform multiple roles, from development and design to marketing and customer support. This model significantly reduces startup costs and eliminates the need for large initial investments or venture capital. It empowers founders to maintain full control over their company and pursue growth at a sustainable pace.

I was able to transform myself into a Fullstack JavaScript Developer in a short amount of time, using GPT-4 + NextJS + Clerk + Stripe + Vercel ai SDK + Sonny Sangha on YouTube and codewithantonio on YouTube.

The advantages of this model are manifold. Solo founders can make decisions swiftly, pivot without bureaucratic delays, and retain a clear vision for their company. This approach also allows for a healthier work-life balance, as founders can dictate their own pace without external pressures. Ultimately, it leads to a more personalized, passion-driven approach to business, with the founder's unique touch evident in every aspect of the company.

Technological Enablers

Key to the rise of the one-person startup is the availability of advanced technologies, especially Large Language Models (LLMs) like ChatGPT Plus. These AI tools provide entrepreneurs with a breadth of knowledge and capabilities, from coding assistance to business advice. They effectively act as a virtual team, supporting the solo founder in areas outside their expertise.

Other platforms play crucial roles too. Vercel simplifies web deployment, Clerk handles user authentication and management, and Stripe enables easy payment processing. These tools collectively lower the technical barrier to entry, allowing founders to focus on their core product and business strategy without getting bogged down in technical complexities.

Case Study: Maple

My journey with Maple serves as a compelling example of the solo founder model's efficacy. As the sole force behind the business, I managed all aspects, from tech development to marketing. This all-encompassing control was not just about managing tasks; it was about the agility and speed at which I could implement new features. A case in point: introducing referral codes to Maple.

In a traditional startup setting, adding a feature like referral codes would involve multiple steps: discussions with engineering and product management, backlog scheduling, prioritization, development, testing, and finally deployment. This process could stretch from weeks to months. However, as a solo founder, I simply consulted ChatGPT for coding guidance based on Stripe's documentation, reviewed and integrated the code myself, and deployed the new feature—all within a mere three hours. This example starkly highlights the unparalleled speed and efficiency that a solo founder, aided by AI and modern tools, can achieve.

The Future Landscape

Looking ahead, the one-person startup model could become the new norm, especially for college graduates and emerging entrepreneurs. This shift could redefine the startup ecosystem, bringing a surge of innovation and a diversity of new products and services. As technology continues to evolve, the feasibility of running a company single-handedly will only increase, opening the door to a multitude of niche markets and specialized offerings.

This trend could lead to a more democratized and diversified business landscape. We might see a proliferation of specialized, niche products and services, each tailored to specific customer needs and developed with a personal touch. The potential for individual creativity and innovation in this space is immense, and it could reshape entire industries, making them more responsive to consumer demands and more dynamic overall.

Challenges and Considerations

However, the one-person startup model is not without its challenges. Acquiring a broad range of skills can be daunting, and the workload can be intense. Founders must balance a multitude of roles, from technical development to marketing and customer service. Additionally, scalability can be a concern, as there's a limit to what one person can manage effectively.

It's also important to consider the risk of isolation and burnout. Without a team, solo founders must be self-motivated and disciplined. Networking and seeking mentorship become crucial for support and guidance. Moreover, while this model allows for greater control, it also means that all responsibilities and pressures fall squarely on the founder's shoulders, which can be a heavy burden.

Conclusion

The rise of the one-person startup marks a significant shift in the entrepreneurial landscape. Enabled by advanced technologies and driven by individual passion and innovation, this model offers a new pathway to business success. It allows founders to maintain control, grow at a sustainable pace, and infuse their unique vision into every aspect of their company.

As we look to the future, it's exciting to contemplate the potential of this model. It promises a more diverse and dynamic business world, where individual creativity and innovation can thrive. Whether this will become the dominant model for startups remains to be seen, but its growing popularity is undeniable, and its impact on the business world will be profound ...

I think there’s something messed up about the startup culture in the USA. The belief is that you have to work 6-7 days a week and spend all your mental cycles on your company. Nothing but pledging your soul to your startup yields success, right?

Not in my experience.

We work a 4-day week at Treehouse and here’s what we’ve been fortunate to achieve:

1. Profitability (yay!)
2. $3,000,000+ yearly revenue run rate (and growing fast)
3. Grown the Team to 34 full-time people and hiring at least 10 more as soon as possible
4. World’s best investors, including Kevin Rose, Reid Hoffman, David Sze (Greylock), Chamath Palihapitiya (Social+Capital) and Mark Suster (GRP)
5. Coverage in the NYTimes, Wall Street Journal, MIT Tech Review and more
6. A $4,750,000 A-round investment
7. An unbelievable company culture where we’re all insanely excited to tackle our Mission

We work a 4-day week (M-Th, 9-6) because we think that information work isn’t like manufacturing. Another hour at the MacBook won’t yield another $1,000 in profit. We believe that smart folks can get five days of work done in four days. Simple as that.

There are so many benefits to working less it’s hard to list them all, but here are the major ones:

1. Recruiting is easy (we still pay full salaries and offer a very generous benefits package).
2. Retention is easier. One of the Team told me he regularly gets emails from Facebook trying to win him over and his answer is always the same: “Do you work a 4-day week yet?”
3. Morale is boosted. On Mondays everyone is fresh and excited - not jaded from working over the weekend.
4. I get to spend 50% more time with my kids then almost all other dads (three days versus two). Fifty percent. It’s insane. For those on the Team without kids, they get to spend this extra 50% on their hobbies or loved ones. (Hat tip to its_so_on for correcting my math and making it even more awesome :D)

A lot of the teams that are working 6-7 days a week are young without families. I’m 34 and I have two kids. I’m not willing to sacrifice my family and health for my company, even if they are. The great thing is that I don’t think anyone does. So if we can achieve profitability, grow quickly and raise large amounts of capital, all while working 4-days a week, shouldn’t you consider it at your startup?

2010: Think Vitamin Membership Launched

• Treehouse was originally named "Think Vitamin Membership"
• Founded in the UK by Ryan Carson and Gillian Carson
• Think Vitamin Membership offered online training videos to learn web design and web development
• Ruby on Rails app was built by contractor Joel Moss and designed by Carsonified employee Mike Kus
• Bootstrapped with cashflow from Carsonified + small business loan
• Hired the first two teachers, Nick Pettit as a Web Design Teacher and Jim Hoskins as a Web Development Teacher
• Opened small office in Orlando, FL for filming and editing
• Membership pricing: Diamond $99/mo, Gold: $49/mo and Silver: $25/mo

2011: Think Vitamin Membership Re-branded to Treehouse

• Relaunched as Treehouse at teamtreehouse.com
• Raised $600k from angel investors: Kevin Rose, Reid Hoffman, David Sze, Josh Elman, Chamath Palihapitya and Mark Suster
• Hired Alan Johnson as lead developer and scaled team
• Alan Johnson was promoted to title Co-Founder

2012: Treehouse Raised Series-A Round and Moved to Portland Oregon, USA

• Treehouse raised $4.75m from Social+Capital and Greylock Discovery Fund
• Ryan and Gillian Carson moved to Portland Oregon and opened new office
• Team was scaled to 34 full-time people

2013: Treehouse Raised Series-B Round

• Treehouse raised $7m from Social+Capital and Kaplan
• Treehouse flattened its org structure and moved managers into individual contributor roles

2014 - 2015: Treehouse Scaled Team and Moved to New HQ

• Treehouse became known for working a 4-day work week
• Reinstated management layers
• Scaled team to over 100 full-time employees
• Alan Johnson and Ryan Carson sold 10% of company to investors in secondary sale
• Alan Johnson departed the company

2016: Treehouse Revenue Began to Decline

• Revenue growth slowed
• Ryan Carson and Board of Directors decided to end the 4-day week policy to attempt to create more content and increase revenue
• Team reduced by 35%

2017 - 2018: Treehouse Launched B2B Business to Battle Revenue Decline

• Revenue continued to decline
• Launched B2B business to try to increase revenue

2019: Treehouse Reduced Team Size to Lengthen Runway

• Layoff was actioned to control costs and give the company more runway
• Apprenticeship program "TalentPath" was launched

2020

• TalentPath was shut down due to the COVID-19 pandemic
• Revenue continued to decline

2021

• Acquisition by large EdTech company did not complete
• Ryan Carson moved his family to Connecticut after Pandemic
• Board made difficult decision to reduce team from 45 to 18 people, retaining 10 full-time employees and eight contractors
• After layoff, Treehouse received unsolicited offer to be acquired by Xenon Partners
• Sale of company was completed in Dec 2021

Videos about Ryan Carson and Treehouse

Jason Calacanis interviewing Ryan Carson from Treehouse

Kevin Rose interviews Ryan Carson, CEO of Treehouse

The Case for the 32-Hour Workweek with Treehouse Founder Ryan Carson

The Case for the 32-hour Workweek: Atlantic

Since 2006, Ryan Carson, the CEO of Treehouse, has maintained a four-day workweek for his employees. “There’s no rule that you have to work 40 hours, you have to work more to be successful,” says Carson. “We’ve proven that you can take it from an experiment into something that’s doable for real companies and real people in highly competitive markets.” Citing the benefits of a more flexible schedule, Carson believes that the reduced time in the office ultimately leads to an overall more productive work environment. But for Carson, his decision ultimately comes down to priorities. “It’s not about more family time, or more play time, or less work time—it’s about living a more balanced total life,” says Carson. “We basically take ridiculously good care of people because we think it’s the right thing to do.”

TalenPath Apprenticeship Program by Treehouse

Ryan Carson explains 'Who Does What in the Tech industry'

Interview with Chamath Palihapitiya, investor in Treehouse

Chamath Palihapitiya is the founder of Social Capital, a purpose-driven venture capital firm that invests primarily in healthcare, education, and financial services. (Social Capital was a Treehouse investor.) In this interview from 2013, Pasan Premaratne talks to Chamath about the reasons behind his investment choices and some of the challenges facing entrepreneurs.

Articles about Ryan Carson and Treehouse

Treehouse CEO Ryan Carson Builds a 21st-century Trade School

Oregon Business article about Ryan Carson, CEO of Treehouse

Ryan Carson, CEO of Treehouse, voted Entrepreneur of the Year

In 2015, I was voted Entrepreneur of the Year by EY.

Treehouse Student Success Stories

Joe

Joe had always thought you needed to fit a certain stereotype to be a developer. When he realized there was an opportunity for him to learn to code and make a difference as a developer, he took the risk and switched careers. Since learning with Treehouse, Joe has embraced a rewarding career as a developer.

Bryan

In less than 10 months of using Treehouse, Bryan landed his first full time professional programming job and got a huge increase in salary!

Kavitha

Kavitha was out of the workforce for 12 years and then one day decided to learn to code and 4 months later she had her first app in the Apple App Store.

Lessons Learned and Moving Forward

I launched Treehouse because I deeply believed in democratizing access to computer science education so people could change their lives. I'm grateful to have led the company to teach over 1,000,000 students in 10 years.

As time progressed, I learned hard lessons about the importance of focusing on profitability and maintaining strategic clarity. I changed the company's priorities too many times, and I take full responsibility for the outcome.

Throughout my entrepreneurial journey with Treehouse, I gained invaluable insights that have shaped me as a leader and innovator. I learned the critical importance of balancing bold vision with pragmatic execution and adapting quickly to changing market conditions. Cash flow management and profitability are key to building a resilient organization.

Most importantly, I learned that trust is the foundation of any successful venture—trust with investors, employees, and customers. I am committed to applying these lessons with humility, transparency, and a steadfast dedication to creating value for all stakeholders.

As I move forward in my career, I am excited to leverage my experience and hard-won insights to build organizations that make a lasting, positive impact. I am dedicated to continuous learning and improvement, always striving to earn the trust of those I serve.

Like most entreprenuers, I believed I needed to sell a company for a pile of cash in order to be successful. I’m not sure why I felt like this. I believe it was related to reading about acquisitions in the news and blogosphere. You’d see a photo of a smiling entreprenuer and read about the millions he just made from Google buying his company. It felt every company was in a sports league and winning the championship was being acquired.

I read the E-Myth and soaked up every word, believing it to be Gospel. I was continually engineering my company to make it run without me so I could sell. I imagined what it would be like to announce the aquisition and then see all those zeros in my bank account.

Well, selling your company doesn’t make you happy and you don’t feel like you’ve reached the summit of your career or life. It’s just another stop on the journey.

Yes, the extra money is useful for things like paying off your mortgage and giving you more financial freedom, but it doesn’t change who you are fundamentally. If you’re reading this post then you’re already richer than a huge portion of the world, so selling your company isn’t going to fundamentally change your existence. You already have a laptop, an internet connection and some sort of education. You already crossed the poverty line.

After you sell your company, you wake up the next day the same person. You drag yourself out of bed, bleary eyed and start the coffee maker. Your kids still wake you up too early and you still have to do your household chores. It’s all the same. You don’t just sit back and relax. But the truth is you don’t want to coast. You want to keep moving forward.

Every entrepreneur wants the following things and selling your company doesn’t change them. You want to be …

1. Solving a problem that makes the world better
2. Working with people you like and respect
3. Free to be creative
4. Hitting milestones and making progress
5. Challenged and learning

Running Treehouse meets all of those requirements for me. I am having an absolute blast and I have no intention of selling the business. If Treehouse was the last thing I did in my career before I died, I’d feel 100% happy.

I’m doing something that matters and I love it.

My advice is to examine your thoughts and see if you’re waiting to sell your company in order to be truly happy. The truth is that you’re probably already as happy as you’ll ever be and selling your company won’t change that.

Do your best to ignore TechCrunch and their non-stop acquisition chatter. The media is run by journalists, not entrpeneurs. Companies being bought and sold generates pageviews, but has very little to do with you and what you set out to do with your company.

Selling your company isn’t actually what you’re striving towards. As a wise man once said “These are not the droids you’re looking for.”

Enjoy the adventure that you’re currently experiencing and realize the daily highs and lows are what actually make your life meaningful.

Have you sold a company? Has the experience made you happier? Please leave your comments below - would love to hear your thoughts.

https://x.com/ryancarson/status/2008548371712135632

https://x.com/ryancarson/status/2016520542723924279

https://x.com/ryancarson/status/2018354837918732297

https://x.com/ryancarson/status/2020931274219594107

https://x.com/ryancarson/status/2023452909883609111