The inspiration to set up a remote development environment hit me when I saw my colleague Eric logging into his remote desktop PC at home through his Chromebook. If you’re comfortable on the command line and aren’t afraid of working in Linux, then why not make your whole development environment remote? It’s 2018 for goodness’ sake!
In this post, I’ll outline my experience setting up and using a remote development environment with DigitalOcean and Google Chrome. I’ll cover the apps I used to make remote development workable as well as some of the tradeoffs of going this route. You could replicate this environment on a Chromebook, Macbook, old laptop, or even a tablet (with some different apps).
First, let’s talk about why you would want to go through the process of developing on a remote machine. There are certainly some tradeoffs - I’ll talk about the cons toward the end of the article - but here are the advantages of a remote work environment:
Don’t have your computer with you, but you want to make a quick code change? Want to do remote development from an iPad or even your smart phone? This set up allows you to have access to your dev environment anywhere you have an SSH connection, meaning any terminal, Chrome web browser, or even a mobile app.
A new Macbook Pro will set you back up to $3000, but if you can do your dev work on a Chromebook and a Digital Ocean droplet, you can spend less than $200 up front and $40/month or less to keep your environment running.
I almost always work with Linux servers, and while 95% of the time, there’s no real difference between them and my Mac OSX, it’s nice to know that my development environment accurately mirrors our server’s. It has also forced me to get better at working with servers and bash scripting.
Having an issue with your computer? Can’t figure out why your code won’t compile? A remote development environment will allow you to give other developers direct access to your machine if you so desire. Just add their SSH key or set them up with a user account with limited access. Just don’t forget to remove it when they’re done.
As more of our tools go to the cloud, I think it’s reasonable to assume that more of our computing power will too. The economies of scale and awesome tools for virtualization are making it cheaper to get server space, and with the internet being available just about everywhere, connectivity is becoming less of an issue.
As I got into researching this project, I realized I was far from the first person to have this idea, so there are a ton of great tools and guides out there. After trying a few tactics, here’s the process I used to get a remote environment running. You may want to tweak this by trying a different hosting provider or different Chrome apps, but hopefully this gets you on the right track.
DigitalOcean’s droplets are virtual private servers that range in price from $5/month to $160+/month depending on the size and bandwidth you need. Each one comes with a public IP address, hard disk, and network connectivity, so it takes about 60 seconds to get a server up and on the internet. You can create them with a bare Linux install or with a one-click application that comes pre-configured to common project specifications. Let’s take a look at how easy it is to set one up.
I like using Docker for development, so I chose to set up my droplet using the Docker one-click app. If you prefer to use a LAMP stack or you build a lot of Node apps, you might want to select those presets. Otherwise, just pick your favorite Linux distro.
Chose a droplet size. The one I picked has 4GB of ram and 2 CPUs since my remote environment is used only for development and doesn’t need to run many high-memory jobs. DigitalOcean won’t let you scale a droplet down (but you can scale it up), so it’s better to err on the side of smaller and then crank up the power if you have to.
When you select a region, it’s best to use one closest to your physical location. This will ensure that the connection is not bogged down by regional lag. If you do need to do a lot of global traveling, you can take a snapshot of your droplet and redeploy it into a new region in just a few seconds.
Next, get your public SSH key and add it to the droplet. This allows you to SSH into the server using the root
user.
Name your droplet and click create. Within 60 seconds, the droplet should be up and running!
Finally, from a terminal, create a new non-root user (to prevent security issues), and then give the new user an SSH key so that it can connect with remote services and servers.
Up to this point, everything has been done in DigitalOcean’s GUI and your bash terminal, but in order to make this remote environment completely remote, we need to be able to access it from Google Chrome. My goal was to do anything I could from my command line in a web browser. This means finding a text editor or IDE, a shell terminal, a way to interact with my APIs, and a way to see and edit items from my databases (usually MySQL).
After trying several Chrome Apps, I ended up landing on these four.
Codeanywhere is a web-based integrated development environment (IDE). It’s not as good as PHP Storm, but it’s a step above Sublime for editing real code. So far it’s the best Chrome-based IDE I’ve found so far.
After adding the Chrome app and creating an account, you can right click “Connections” and click “New Connection” to add your server.
Name your connection, use your droplet’s IP address as the hostname, and select Public key. Click “Get Your Public Key” at the bottom, then add that public key to your new droplet.
After you connect, you should be able to edit files, create folders, and do pretty much everything you would normally do in a local development environment - all in your browser.
At first I tried using the bash shell built into CodeAnywhere. Unfortunately, it’s lackluster and slow, so I opted for a separate terminal and found Chrome Secure Shell.
After you install the app, you’ll need to add a connection to your droplet here as well. Add your user and IP address into the appropriate fields.
At first it wasn’t intuitive, but when you import your SSH keys, you have to select both your private and public id_rsa
keys.
Once your id_rsa
keys are added, click Connect and start using the terminal just like you would on your local machine.
If you do a lot of work creating APIs, you need a way to test requests. I’ve been consistently impressed by Postman as they’ve continued to innovate over the past 3 years that I’ve been using the tool.
It’s pretty simple to install Postman and start creating requests, so I won’t go over that in detail, but connecting to your new droplet is easy. Just use the IP address as the URL.
I typically use MySQL as a database, and found Chrome MySQL Admin to be a satisfactory option. It’s not perfect, but I can always write SQL in the terminal if I have to.
That’s it! You should have a workable remote development environment completely usable through Google Chrome apps. If you get stuck, feel free to leave me a message on Twitter and I’ll see what I can do to help.
As promised, I do want to acknowledge the negatives to taking this approach to development. While I haven’t gotten to a point where I’m doing all my dev work on a remote server, I have switched a number of my side projects over, and here’s what I’ve encountered so far:
If you don’t lock down your server, anyone who knows the IP/web address can see your projects on the web. If you need to expose the projects to an open port, the I’d recommend using Apache’s basic auth or locking down the IP addresses that can access the site.
Obviously you must be online for this approach to work. This isn’t really a problem since I have to be online to do just about any development work anyway, but if you’re used to working offline this approach may frustrate you.
For a high-end DigitalOcean droplet with 16GB of ram, you’ll spend $80/month. At that price, you could finance a Macbook Pro over two years and have something to sell back at the end of it.
Having your development projects in a convenient remote location gets you a lot more than just an easy way to develop on any machine. Here are some other reasons you may want to try this approach:
If you’re looking for more Macintosh remote working tips, check out this article on how to screen share on Mac.
]]>While binary classifications are inherently flawed when comparing complex human behaviors, I have noticed that when giving employees feedback, they tend to fall into one of two camps:
those who say they want to improve and those who show you that they do.
As you might guess, I want employees who show me they can respond to feedback and make improvements, but if you’re having trouble identifying them, here are some things I’ve noticed:
The passion for stretching yourself and sticking to it, even (or especially) when it’s not going well, is the hallmark of the growth mindset. This is the mindset that allows people to thrive during some of the most challenging times in their lives.
Carol Dweck, author of Mindset: The New Psychology of Success
When you read the list above, it should be pretty clear that “showers” are easier to manage, more reliable to work with, and typically better hires, but how can you select for these traits? What traits are you even looking for?
I used to spend a lot more time worrying about the technical knowledge my hires had, but in practice, I’ve found personality traits and work habits to be more important indicators for success:
Unfortunately, you don’t always get to pick your team, and sometimes you bring on someone who turns out to be tougher to manage. I’m a firm believer in giving people a chance, but you also have to set them up to show you marked improvement.
Here are some general tips that I’ve found helpful for helping employees become “showers”:
Whether you’re reading this as an employee who wants to show their boss they can respond to feedback or as a manager who is giving this feedback regularly, I hope it helps to think in terms of “showers” and “sayers”. If you want to continue to the conversation, find me on Twitter.
]]>Here’s the original question:
I am a sub contractor for an agency but the ISV is small and doesn’t have many insights into software used and deficiencies in it. So my ask is, are there any gaps in the software you currently use? Things that you wish were better but can’t see yourself spending your own developers time on them?
I am still hunting for my saas idea and was wondering if any of you have come across something that you just didn’t want to tackle but you know could be a good saas if given time to develop.
Ultimately, you can boil this down to two questions:
First off, modern digital agencies use a lot of software. I run a couple agencies, and while software exists for everything I need to do, it could always be improved.
The industry of software that serves agencies is huge and there is a lot of competition, but competition isn’t a bad thing. Competition means that there are active buyers looking for solutions. Every year, these buyers are looking at their bottom lines and reconsidering their software spend based on which tools actually drive the most value.
Selling to agencies also has some major advantages for SaaS founders. First, it’s a B2B sale, meaning you can likely sign long-term contracts and have larger deal sizes than in consumer software.
Second, it’s easy to find agencies. They want to be found by their customers, so vendors looking to sell to them should have no issue finding them on social media, email, or even in-person events.
Finally, agencies tend to have high turnover. While this could be bad, it can also mean the tools you build will spread as former agency employees leave and pick up jobs or start new agencies.
While there are a lot of reasons agencies make good SaaS customers, I don’t want to paint an overly rosy picture. The challenging part about building a SaaS for agencies is that competition is high and the switching costs for existing solutions might be very hard to overcome.
For example, if a vendor came along with a perfect project management tool, but our existing tool was good enough and the migration would take many months and thousands of dollars in employee time, I probably wouldn’t switch. Convincing agencies to spend time on non-billable work (which lowers their margins) is an uphill battle.
You can get around this by tailoring your SaaS to new agencies, but these are typically the most volatile and price sensitive ones. So, while I think building software for agencies is a great opportunity, it’s not without its challenges and it’s important to know what kind of problem you’re solving.
Assuming you’re ready to tackle this market, you need to figure out what you’re building and for whom.
The digital agency market is huge and highly fragmented, so you need to narrow down the type of agency you want to serve: a 2-person agency is much different from a 200-person agency, and they rarely have the same needs.
You might also want to segment your customer discovery by industry. Agencies that service small, local businesses will have much different needs and employee profiles than those that serve high-growth tech companies or large enterprises. Similarly, advertising agencies will have different needs from copywriting agencies. Getting as clear and specific about your target customer as possible will make answering this question much easier.
Once you’ve started to figure out your ideal agency customer, you can start to explore the types of software they use and some of the challenges each presents. The key is to find software that they’re using but underserved by in some way.
Here are some areas to explore:
While I’m not planning to build a SaaS anytime soon, I do think that agencies make good SaaS customers. They’re easy to find, open to long-term deals for discounts, and less price sensitive than individual consumers.
But I’d love to hear what you think. If you have experience building or selling a SaaS to agencies, let me hear about it on X.
]]>Because marketing is an afterthought, the only go-to-market work these founders do is to set up a landing page and some cold email sequences. So, their first clients all come in through cold outreach. Clients won through cold outreach tend to be the most price-sensitive, fastest to churn, and toughest to please, so the entrepreneur spends all their time servicing these clients instead of building sustainable, inbound marketing channels.
And despite what gurus tell you, cold outreach doesn’t scale well.
If you don’t have extremely specific personas, great messaging, supporting collateral, or good client disqualification methods, most of your outreach will be wasted and contribute to poor deliverability scores. So again, the entrepreneur is stuck on a hedonic treadmill, trying to find new prospects, offering pricing discounts to win business, and neglecting long-term marketing assets.
Finally, cold email and Linkedin outreach will only get harder as the channels become more saturated. The volume of junk I’m getting on both channels has increased markedly in the past year, and because these are non-monetized avenues for the platforms (ie: Gmail and Linkedin don’t make money off cold outreach spam), they’ll inevitably make them harder to use as time goes on (case in point, Google is doing it this year).
There are two ways that service business owners can break free from the cold sales trap I’ve described above. Unfortunately, both require patience and discipline, which first-time entrepreneurs often struggle with. That said, they both work and can be used in combination to close higher-quality, higher-margin clients than cold outreach does.
Our very first large corporate client at Draft.dev came in because of a Linkedin post I shared about how my small business was enabling me to have more time with my son.
Sharing success stories from clients, the impact you’ve had on employees or the community, and the processes you’ve built will all lead to far better long-term clients than cold outreach will. This can be done on your blog, social media, newsletter, niche communities, etc. The key is to change your mindset about advertising your business and instead of constantly asking for others to help you, start sharing what you know.
Sharing value for free attracts high-trust clients and allows you to have fewer clients that pay you more.
Having great content to share is important, but as they say, “If a tree falls in the forest and nobody hears it, does it make a sound?”
Entrepreneurs that don’t know where their prospective clients congregate or have no access to these places have a fundamental business problem that they need to solve before they start. If you can’t find 20 prospective clients to have a conversation with before you launch, you need to go back to the drawing board.
And 20 prospects is really all you need to get started. Assuming you can make $1000+/month from each client, 20 is a great base to build from.
So, if you’re creating great content that would be helpful to your prospective clients and you spend time with them (online, in-person, doesn’t matter), you’ll have plenty of opportunities to share. Then, leverage that sharing into conversations about their needs, and when the time is right, talk about what you do.
It sounds simple because it is. It’s just not easy for many because it involves getting out of your comfort zone. You have to get away from the wannapreneur support communities for a bit and talk to real businesses that can buy from you.
Absolutely. We win nearly 30% of our new clients from cold emails at Draft.dev, and plan to continue using it for the foreseeable future. But, it works well for us because we are very sure of our ICP (Ideal Client Profile) and use a very targeted, low-volume approach.
As an established brand with hundreds of clients and thousands of sample pieces published, we also have lots of supporting collateral to bolster our outreach. This means that even skeptical prospects can verify our reputation and previous success.
As a part of a multi-channel marketing strategy that includes content, supporting collateral, and social proof, cold outreach is a fantastic growth lever.
As your only attempt at kickstarting a trusting client base with sustainable margins, cold outreach is a terrible trap.
]]>The list goes on.
Every day, I wanted to wake up and work on interesting things, but my energy was sapped by a hundred small choices that I had to make in order to keep from blocking my team, customers, or family.
As I reflect on the hundreds of conversations I’ve had with entrepreneurs and aspiring entrepreneurs, decision fear and decision fatigue are two of the biggest things that hold entrepreneurs back.
So, I want to address these two mental hurdles and how I’ve managed to (mostly) overcome them.
Successful entrepreneurs use focus and leverage (skills, money, relationships, etc.) to maximize their impact. Decision fear keeps entrepreneurs from picking a path and focusing.
This is why I spent the first ten years of my career with a day job and lots of half-baked side projects. The choice to start a business and go full-time on it feels massive and irreversible (it’s not, but it feels that way).
I started reading The Top Five Regrets of the Dying recently, and the number one regret is not having the courage to live a life true to yourself. Author Bronnie Ware puts it this way:
“When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.”
Fear is a complicated emotion, but one of the byproducts of overwhelming fear is the inability to take action. This comes from believing that making a choice might make the fear worse, so many people never take the actions they’d need to to overcome the fear.
“In every situation, life is asking us a question, and our actions are the answer.” - Ryan Holliday, The Obstacle is the Way
Developing a bias towards action is the only way to overcome decision fear. You have to learn to live in the moment and make the best choice you can with the information available, ignoring the million possible roads you could have taken.
For some, decisiveness is easy, but for others, this is an impossible task. What worked for me was starting relatively small and growing into bigger and bigger decisions.
When I started my business, I told myself it was just a temporary thing to do between jobs.
As it started to grow, I told myself it was just a lifestyle business that would allow me to spend more time with my family.
And now, I see it as the cornerstone in a 10-year project.
Along the way, I told myself the gravity of my decisions was just as small as my aspirations, but as you can see, the gravity grew as I became comfortable with it.
Decision fear affects people at all stages. I know entrepreneurs with businesses 10x bigger than mine who are deathly afraid to make certain hires, change their role in the business, or fire key people.
Not making decisions will only hold you back, so build a bias towards action.
There are a lot of decisions in running a small business, so your goal should be to make only the most crucial ones every day.
Decision fear has gotten easier for me over time, but fatigue is still something I have to work around on a daily basis. Tiny decisions suck up my willpower, so I try to build my day around making just a few of them.
I delegate almost any decision that doesn’t have 5-year consequences.
For example, my Account Director asked me what we should say to a particular client request recently. While the request wasn’t unreasonable, it technically was out of scope. Should we say yes? Should we start a new service based on the request? Should we just decline their business?
There’s no right answer, but the choice was small enough that I couldn’t imagine it dramatically hurting or helping our business in five years either way. I told him to ask the production team for their opinion and then move forward with the choice he thought was best.
I didn’t have to spend any of my precious decision-making energy on the decision, and I don’t think my business would have been better if I had.
Even small, personal decisions like what to eat or what to wear add up.
To cut down on these, I write down my meal plan every week instead of deciding what to have each day when I get up. Knowing what I need to have in the house and what I’ll eat for lunch each day keeps me from having to fight the urge to run out for fast food (a bad decision) because I’m just too sapped to make a good decision.
Build your life around making only the most important decisions and you’ll have the mental energy and clarity to make them even better.
Entrepreneurs who act decisively and focus relentlessly give themselves the best chance at making a really big impact. Decisions must be made, but you can’t let looming decisions sap your energy.
]]>Let’s start with a brief example…
I recently finished More Awesome Than Money, a book about the college students who started Diaspora, an open source, privacy-focused answer to Facebook. As a business, Diaspora was never very impressive, but its message resonated. They raised over $200,000 from Kickstarter and ended up with over half a million users at their peak.
With such a successful launch, you’d think that Diaspora could buy enough time to figure out how to grow the project and make a viable business, but it’s not that easy. Being decentralized meant that they couldn’t really charge users (at least not all of them) and it worried traditional investors who wanted to see a plan for monetization. Additionally, the founders were inexperienced college students who struggled to retain good employees and managers.
The social network eventually met a slow, tragic end with one of the founders committing suicide and another heading back to college. The remaining founders ran out of money and while the codebase is still under active development, it runs as a non-profit that is largely supported by its contributors.
“People engage in creative endeavours because it satisfies some deep need within themselves to exercise creativity and solve problems often with little regard to the societal benefit.” - James Bottomley, Distinguished Engineer at IBM Research
To be honest, most open source projects aren’t started for money.
James Hickey, founder of the .NET Coravel project, which has over 2 million downloads and 2800 stars on Github, told me he started the project because it “seemed to me a missing piece of the .NET ecosystem.” While starting the project helped James solve his own problems and learn more about the language itself, Coravel also proved to be useful to many other programmers.
But maintaining a large open source project is a lot of work. While James has successfully monetized Coravel, many open source developers never make much money from their efforts. Let’s take a deeper look at why this is so hard and how some companies are overcoming the challenge.
An open source company as any business whose primary product is open source software.
Open source software is distributed publicly, typically for free, but because maintaining software is a lot of work, many of the largest open source projects are supported and owned by for-profit companies.
A well-known example is Automattic, the parent company that maintains and distributes WordPress.org. While Automattic now runs several closed source software products in addition to the open source WordPress, they started primarily as an open source business.
Red Hat, the maintainer of one of the most popular Linux distributions, is another example of a large open source company. While they continue to build some free, open source solutions, they offer high-touch services and remote support to maintain the business.
Strapi is also an example of an open source company. I recently asked Strapi’s Head of Marketing, Victor Coisne about why they give away the core Strapi product and he mentioned four things:
Building a business around an open source project can be really hard. Emily Omier, who helps open source companies with positioning and commercial strategy, has built her business around helping open source companies address some of these challenges. She pointed out to me that the decision to make a project open source is not one that founders should take lightly:
“Not all open source companies start with an open source project that is then monetized…often the founders start with an idea, and decide that the best way to build the company they want to build is with an open source approach.”
She pointed out that one of the biggest challenges open source companies face is that by monetizing, they might seem like they’re trying to “wring dollars out of the open source community,” which is not a good approach. “Often the people who are good commercial customers would not be part of your open source community.”
Open source companies must understand the different drivers that contributors and potential commercial users have because they likely aren’t exactly the same.
So if the source code in open source software is available to anyone on the internet, why does anyone pay for it? While much open source software is free, that’s not necessarily the case as many different licensing schemes are available.
I’m not a lawyer, but I’ve built enough software to understand that just because code is available on the internet doesn’t mean you’re necessarily allowed to use it any way you want. Similar to how images are subject to copyright even though they can be viewed online, code is also copyrighted by default. You can’t just copy a nontrivial codebase and use it in your application without permission.
Some open source licenses come with restrictions. For example, some require you to make any software you build with their code open source as well. Others are open source, but not free for for-profit enterprises to use.
Now, let’s not be naive. Once software is out in the public domain, some people will steal it, and they’ll likely get away with it. So, most open source companies choose not to use a license as their primary means of monetizing their software.
Let’s take a look at some of the ways open source companies can successfully monetize, and some examples of companies that have used these strategies successfully.
“[There have] only been two successful models for monetizing open source. One is the public cloud model (…offering open source as a service) and then [there is] Red Hat’s model, which is to be a significant contributor and offer on-premises [software] and drive roadmaps for customers.” - Jim Whitehurst, CEO at Red Hat
While Jim might be right about there being two primary business models for open source software, I think there are enough variations that it’s worth mentioning a few more. I’ve worked with several open source companies in the past (as a contributor, service provider, and consultant), and I’ve seen six ways that they can make money:
While not typically used by large for-profit companies, some individual developers make pretty good money by taking donations for their open source work. Patreon, GitHub, and Buy Me A Coffee are all popular platforms that allow individuals and businesses to help support open source projects that they use or want to see maintained.
The downside to this model is that it’s really hard to build predictable, sustainable income from it. Some people will heavily use and benefit from updates while never paying the creators, and this frustrates those who do support the project. If you’ve ever asked your boss if you can start paying for some of the free, open source software you use at work, you know how tough this can be to sell.
“I think this model works best for smaller-scope projects which are not designed to grow over time,” Victor Coisne told me.
While donations probably won’t take your open source company far, open source projects allow you to run their software on your own servers for free, but they’ll charge you for a hosted version. For example, you can deploy n8n.io to an AWS or DigitalOcean machine and keep it running on your own, or you can sign up for their hosted version and avoid the hassle of maintaining servers.
While this tactic won’t work for every open source project, it’s a very popular option. It offers a clear delineation between the paid and free versions of the product, and can be bundled with other features like support and training. The downside is that your margins are never going to be very high. If you charge too much, users will be able to justify the cost of maintaining their own servers.
Red Hat’s model of open source software financed by paid support contracts and on-premise configuration takes more human hours, but it allows them to improve the user experience dramatically. When companies look at the cost to troubleshoot open source software, it’s usually a better deal to sign up with the people who made the software rather than learn it themselves.
If you want to make your software more accessible, you can sell training at a lower cost than hands-on management and support. For example, The Linux Foundation helps maintain hundreds of open source projects and makes money through its training courses.
Adam Wathan started Tailwind UI as an open source CSS library in 2017. After two years, he went full-time on the project and has now made $2 million in revenue from the project.
While Wathan’s story is exceptional, it highlights how a free, open source project can make real money by charging for extras (in Adam’s case it’s premade UI components). I would call Tailwind an open core product because while the framework and features are all free, you can support the project and save yourself time by buying extras.
Some open core projects do this by charging for features that larger customers are more likely to need like advanced user management, specialized integrations, or SAML access (there was a good thread on Indie Hackers about this model recently). This is a solid strategy if you know enterprise users will need certain things that individuals and small companies won’t.
Similar to the open core model, some open source projects offer a dual license. This might allow a small, independent developer to use the software free, but companies using it for a profit must pay a license fee. For example, Qt offers a dual license:
“Qt for Application Development is dual-licensed under commercial and open source licenses. The commercial Qt license gives you the full rights to create and distribute software on your own terms without any open source license obligations…Qt for Application Development is also available under GPL and LGPLv3 open source licenses.”
Companies can decide which license is appropriate and pay Qt as needed. While some companies might abuse this license structure, lawyers will look at things like this in detail if the company ever decides to sell or go public.
As in Automattic’s case, they offer a free, open source product (WordPress.org) and a suite of related and unrelated proprietary products to generate revenue from. This model is easiest to manage if your other products support the open source one, but some companies raise money from venture capitalists to fund the open source tool’s growth while they figure out other products to build.
The downside to this model is that building and maintaining multiple products is a lot of work. Small teams will find this distracting and it might mean the open source product suffers.
The reality is that many open source companies use multiple monetization channels. Jonathan Reimer, Co-Founder of Crowd.dev told me that they make money from offering a hosted version of their tool and an open core model. “Both of these come with additional features,” he told me. “The key value driver is the intelligence that we add to the data (enrichment, sentiment analysis, conversation detection, etc) in our paid versions.”
If you’re interested in building a profitable open source project and you want to learn more, I’d suggest a few resources:
Note: This piece was first written in 2021, but updated in 2023 with input from several clients and friends in the industry. If you have your own resources or recommendations, I’d love to hear them. DM me on Twitter or Linkedin.
]]>That’s the perception I feel like I’m “supposed” to put out there - that I’m effortlessly successful, perfectly happy, completely healthy, and mentally stable all the time. I don’t share my sleepless nights, my fear of failure, or my struggles with food or alcohol because I don’t want to elicit sympathy or make it seem like I’m begging for attention.
That said, I’ve been trying to open up more about my struggles privately this year.
An old friend recently saw my appearance on Starter Story and reached out.
“Sounds like you’re doing great. I’m so happy for your success!” he said.
I didn’t know where to begin. No, the video didn’t lie. In some ways, I’ve been incredibly successful in my career thus far. But it didn’t tell the whole story either.
2023 has been the hardest in my life so far, both personally and professionally. I don’t want to dramatize this and pretend that my life is hard. I’m extremely fortunate compared to most of the world, but mentally, the past 9 months have been far from the easy road you see on the outside.
And yet, it’s been the year in which I’ve learned the most as well.
I’ve learned more about myself, running a stable business, hiring, and motivation in the past 9 months of struggle than I did in the first two years of building Draft.dev.
In the interest of transparency and to let all the other entrepreneurs out there see it, I struggle too.
Our second child was born in late 2022, and after three months off, my wife went back to work. Leo was cute and healthy (yay!), but he wasn’t a great sleeper. I probably averaged 5-6 hours of sleep per night for the first eight months of 2023.
Due to staffing shortages, the home daycare we planned to put him in was unable to take him right away, so from January to April, I took 2-3 days off work every week, with a nanny filling in the other three.
We’re extremely fortunate that we could find and afford a nanny for a short-term contract, but this was not an expense we had planned for. I also didn’t plan on cutting back my hours at work so dramatically.
This reduction in hours wouldn’t normally be a problem (my goal is for the business to run without me), except my main business, Draft.dev, was simultaneously taking a huge hit. Market forces were impacting our clients (tighter venture capital funding, higher interest rates, and lower technology company valuations), and forcing them to cut marketing budgets.
Draft. dev’s monthly revenue was down 50%-75% of its peak in 2022, and it became clear that demand wasn’t going to bounce back quickly.
I had to let go of over half the team. It was brutal.
I had several great team members who I just couldn’t afford to keep, but it was heartbreaking knowing that we had worked so hard to train and onboard them, only to let them go during a big tech downturn where it would be very difficult to find a new job.
The process of acquiring The Podcast Consultant was too far along to stop by this point, and it closed during the lowest point in Draft. dev’s downturn.
I had envisioned spending 90% of my time on the new company, but because I had to cut the team so much, I was forced to step back into a sales role at Draft.dev too. I even spent a fair bit of time this summer editing and tech-reviewing content again.
I don’t mind working hard but keep in mind that during this same period, I was watching one kid a couple times per week, sleeping around 5 hours per night, and cutting my own paycheck as much as I could afford to.
As all this work stress was building, our dog (who we’ve had longer than our kids) started to get aggressive towards our oldest son. She attacked and bit him, completely unprovoked, so my partner and I decided we had to rehome her.
It was gutwrenching, and I still cry when I talk about it with my family.
Obviously, most of these stressors were circumstances outside of my control, but I can’t claim to be blameless either.
I wasn’t making time to work out (normally something I do 3-5 times per week), meal prep, or even take regular walks, and that just made the mental fatigue worse. I had few outlets and this led to me drinking more (and more frequently) than I normally would.
Many people in my professional life don’t know this, but I spent 8 years after college sober. I was running a lot and very focused on my health. After some injuries and having kids, I started drinking occasionally a couple of years ago.
But, when the stress picked up this year, I found myself struggling to moderate. One of my strengths is my obsessive, competitive personality, but I believe it also makes me susceptible to substance overuse. I never got into hard drugs, but when I am at a party drinking, I want to keep up with the best of them. (As an aside, I’ve since quit drinking completely and am 100x happier for it).
Unfortunately, poor habits beget poor habits, so this cycle worsened throughout the first half of the year. Lack of sleep, lack of exercise, bad diet, and drinking too much led me to sleep worse, exercise less, eat worse, and drink more.
Fortunately, I saw this cycle of decline, and it was pretty clear where it was going.
Despite all my flaws, I have a high level of self-awareness, and I do not suffer from a depressive personality. My natural optimism lends me to solutions-oriented thinking rather than allowing negative feedback loops to continue, so soon after I recognized the problem, I started to look for ways to address the factors that were within my control.
In August, things started to stabilize. It’s hard to say what came first, but I believe it’s all linked in some way:
In hindsight, 7-8 months doesn’t seem that long, but when you’re in the depths of it, it can feel like a neverending nightmare. That said, now that it’s behind me, I can take stock of the experience and I’m very grateful to have had it so early in my entrepreneurial career. Here are just a few of the things I learned this year:
Taking the path of entrepreneurship is not easy. There were days this year that I wished I could ignore work, but unlike a regular job, you can’t just leave it at the office.
If you’ve been through struggles and you want to share them, or this helped you in any way, let me hear about it. Find me on Twitter/X.
]]>The problem is that the impact of a book is dependent on your current situation and challenges. The books that impact me most now probably wouldn’t have been helpful earlier in my journey, and the ones I read when I was first starting out probably wouldn’t be as impactful to me personally anymore.
I also read a lot, and many of the books that have impacted my entrepreneurial journey the most aren’t typical business books.
Classics like Good to Great and Measure What Matters are great all-purpose business books and will help you be a better manager, but I find their application to entrepreneurship pretty weak.
With those caveats aside, I thought it would be interesting to share the 12 books that have had the biggest impact on my entrepreneurial journey. I’ve organized this list chronologically, so I’ll explain each book in the context of its impact on my life at the time.
Hopefully, some of these will hit you at just the right time in your entrepreneurial journey to make a big impact too.
After I graduated from college, I spent 6 months living in a tent and touring the Eastern half of the United States. During this period, I had a job with a small startup where - for the first time - my income was removed from my hours. I was paid for producing results, and I typically didn’t have to work many hours each day to hit my numbers.
Needless to say, The Four Hour Workweek appealed to me, but it also made me realize that reaching your goals as an entrepreneur doesn’t have to be tied to working more hours.
This was a pretty new concept to me because most small business owners I knew at the time worked much harder for much less money than I wanted. Reading The Four Hour Workweek gave me permission to work smarter, and helped me realize that by leveraging people and processes, I could maximize my impact while minimizing my time spent actually “working.” It also turned me onto the idea of tracking my time so I could understand what I was actually doing and critically evaluating whether I needed to be the one doing it.
I re-read this book in 2022, and while I still like it, I realize how outdated some of the tactical advice it offers is. That said, I’d still recommend the first half of the book. If you’re interested in how the book has held up, there’s a good episode of Tropical MBA that goes into more detail.
As I was traversing the country in my car, I happened to read another book that I continue to reference and reflect on today: How to Win Friends and Influence People.
While the title sounds cheesy (and honestly, the book is pretty cheesy), I took away more from this book than any other business advice book I had read before. Little things like, “a person’s name is to that person, the sweetest, most important sound in any language” and “the man you are talking to is a hundred times more interested in himself and his wants and his problems than he is in you and your problems” ring through my head every time I have a conversation with a new person.
The bigger my companies and my role has gotten, the more I come back to this book’s advice. So much of my day-to-day now is sales and subtle influence that it’s critical not to loose sight of this book’s basic wisdom.
If you can accept that this nearly 100-year old book uses outdated style and language, you’re in for some of the most important lessons anyone can learn.
After my 6-month stint living in campsites, I spent 10 years working as a software engineer at various early-stage startups. During that time, I read more about engineering and management, but in 2020, I started thinking about leaving my day job to start my own business.
I had seen many startups build products and services that nobody really needed, so as I began to evaluate business ideas, I knew I had to avoid the same mistake.
My good friend, Tony Chan was a few years ahead of me in running his own business and he recommended The Mom Test. This short, pithy book gave me one key takeaway that I continue to use whenever we launch new products and services:
Don’t ask customers what they would pay for. Ask them how much they currently pay to solve their problem and what’s wrong with the solution they’re using.
Getting someone to open up their wallet and spend money on something they haven’t spent it on before is incredibly difficult and it’s the reason most startups never get off the ground. Nobody really needs you to solve the problem, and if they did, they’d be spending money on solving it already.
Instead, try to find a business model that solves an existing problem - with a dedicated budget - better, faster, smarter, etc. It sounds simple, but this advice is rarely followed.
My first business was a technical writing company, and in the early days, I did just about everything myself; I was essentially a freelance writer.
This got me on track to read a bunch of books about freelancing, writing, and creative pursuits, including The War of Art and Big Magic. I grouped these books together because I took very similar messages from both:
Success is a function of doing work, overcoming fear, and persisting in the face of apparent failure.
Both Pressfield and Gilbert spent decades as struggling writers, churning out content that nobody would read or recognize. Both of them mention the fear they had and saw others succumb to along the way. Fear that they were wasting their lives; that they would never figure out how to create something people wanted.
As an entrepreneur, this message still resonates with me.
Most entrepreneurs I know aren’t any smarter than other ambitious people. They don’t necessarily work more hours or have special skills either. The constant thread I see in entrepreneurs is that they overcame fear and kept going despite apparent failure.
I reference Gilbert’s poem to fear all the time, so I’ll quote it here as well:
“Dearest Fear: Creativity and I are about to go on a road trip together. I understand you’ll be joining us, because you always do. I do acknowledge that you believe you have an important job to do in my life, and that your take your job seriously. Apparently your job is to induce complete panic whenever I’m about to do anything interesting – and, may I say, you are superb at your job. So by all means, keep doing your job, if you feel you must. But I will also be doing my job on this road trip, which is to work hard and stay focused. And Creativity will be doing its job, which is to remain stimulating and inspiring. There’s plenty of room in this vehicle for all of us, so make yourself at home, but understand this: Creativity and I are the only ones who will be making any decisions along the way. I recognize and respect that you are part of this family, and I will never exclude you from our activities, but still – your suggestions will never be followed. You’re allowed to have a seat, and you’re allowed to have a voice, but you are not allowed to have a vote. You’re not allowed to touch the road maps; you’re not allowed to suggest detours; you’re not allowed to fiddle with the temperature. Dude, you’re not even allowed to touch the radio. But above all else, my dear old familiar friend, you are absolutely forbidden to drive.”
If you’re on the fence between these two books, Big Magic is probably the better choice because Pressfield goes into some magical stuff at the end that I’m not really a fan of. That said, if you read one and like it, definitely pick up the other one too.
As my business grew and I started hiring people, someone recommended The E-Myth to me.
I knew that I didn’t want to own a business that relied on me forever, but I also had the impression that service businesses were impossible for founders to get out of. I kind of assumed that I’d have to start a SaaS if I ever wanted to run a business that didn’t need me.
Gerber’s book gave me another path: the “franchise prototype.”
The Emyth encouraged me to think of my business as a system and to work on each part of it individually, finding people to fulfill specific roles rather than people who could do everything I could do.
By putting repeatable systems in place, I was able to scale my business very quickly ($0 to $2.5mm in revenue in just two years) while taking a month off completely when my second son was born.
“Failure really can be an asset if what you’re trying to do is improve, learn, or do something new.” - Ryan Holiday
It’s easy to look back at my first three years of entrepreneurship now and see that things went remarkably well, but in the moment, it has rarely felt like that.
Entrepreneurship is full of rollercoaster ups and downs. I kept thinking that if I can just get over this next hill, it’ll all be easy, but that never seemed to be the case.
The Obstacle Is the Way is a reminder that every great success story follows this arc of apparent repeated failure and an eventual apparent success. People on the outside don’t see the struggles that got you through every day, they just see the end result, but when you’re living the challenges, they feel more real than anything else.
That said, facing hard things is the only way to grow.
Quitting when things get tough is a surefire path to mediocrity. Quitting is the easy way; it’s what most people do. Being exceptional requires failure and the temporary pain that comes with it.
Even if you don’t typically like motivational books, this one is worth a read.
As my business started to take off and I got myself out of much of the day-to-day, the next question I had to ask was, “Why am I doing this?”
At some point, every entrepreneur will have to answer this question, but most of them try to put this off for a long time. They might chase short-term goals like increasing revenue or profit, but these pursuits don’t answer the real question: why are you doing this?
I reference Christensen’s other book, The Innovator’s Dilemma, all the time, so when someone recommended How Will You Measure Your Life, I was excited to try it.
The book is much different from his other books; it’s essentially a series of lectures Christensen gave towards the end of his life about success and the meaning of life as he sees it. For me, it was especially interesting to hear how a man whose professional work I respected so much sees the real point of what he’s done.
Ultimately, this book led me on a search for something bigger, which took me on the first steps toward defining my big vision.
I was first exposed to “entrepreneurship through acquisition” a few years ago when I started guest lecturing at Northwestern’s Kellogg School of Business. A few of the students I met were running search funds with the intention of buying a small business that they could then run.
In 2022, as I started to define some bigger goals for myself, I came back to the topic, and decided that acquiring another business would be a faster and more certain way to grow than starting another business from scratch.
Deibel’s book basically lays out the playbook for acquisition entrepreneurship and is especially relevant if you’re looking to buy a service business like I was. It gave us a template that we could apply to our first acquisition and it’s still the book I recommend most when people ask about buying or selling a small business.
Tony Robbins is a polarizing figure. On one hand, he’s incredibly successful, a gifted speaker, and a great storyteller. On the other, it’s easy to poke holes in his logic, he’s a bit verbose, and he’s given some questionable advice along the way (he was onced hospitalized for mercury poisoning because he ate so much tuna).
That said, many of the principles he talks about in Unlimited Power have impacted my operating system as a human. One idea that stands out to me most is the belief, action, results cycle.
While Robbins uses different words, I will try to summarize my takeaway:
I want this cycle on a poster because I think about it every day.
I’ve always been a high achiever, and like many acheivers, I don’t like to fail or miss my goals. This tends to lead me to setting goals that aren’t ambitious enough as a way to shield my ego.
While I’m still working on this, The Gap and the Gain helped me shift my perspective. The takeaway for me was that if you set a big goal and don’t reach it you have two options:
Seeing the gap without seeing the gain will lead you to constantly chase more and never be happy. Appreciating the progress you make will allow you to enjoy the journey much more.
I love a good allegory, so while friends have been recommending this book to me for years, I finally got around to it in 2023.
The Alchemist is the story of a young shepherd’s journey to find his “personal legend,” a great treasure that is revealed to him in a dream. Along the way, he meets others on the search for their personal legends and learns some universal truths about belief, fear, and having your own great pursuits.
As I’ve been on a journey to define my big vision this year, the book hit me at just the right time.
Some of my takeaways from the book include:
“People are capable, at any time in their lives, of doing what they dream of.”
“When you want something, all the universe conspires in helping you to achieve it.”
“There is only one thing that makes a dream impossible to achieve: the fear of failure.”
“Everyone seems to have a clear idea of how other people should lead their lives, but none about his or her own.”
“There is only one way to learn… It’s through action. Everything you need to know you have learned through your journey.”
If you like this kind of inspirational advice in story form, The Alchemist needs to be next on your list.
I’ve always got a full backlog of books that people recommend to me, but I’m also always keeping an ear out for others. Find me on Twitter if you have your own suggestions or you liked this list.
]]>It sounds simple, but most small business owners never reach that point. Most are notoriously overworked and underpaid.
In 2021, I set myself up to take a week off completely. I blocked off my calendar, set up an autoresponder, and spent a week completely unplugged from my business. It was great, and it really helped the team see that they didn’t need me as much as they thought.
When we found out we were having our second baby in 2022, I started to plan my month off. By that point, we had a salesperson, Account Director, and Operations Director who could handle pretty much everything without me. In October, 2022, I put my autoresponder on, and checked out again.
Most ambitious people think that reaching your goal will free you, but that’s not really what happens.
I was running a relatively successful small business that I could take a whole month off from at a time, but more than ever, I felt like I wanted to do something more.
First, I thought about selling it and taking some time off. But, honestly, what would I do with a year or two off? Probably start something new, so why take two steps back?
So instead, I went the other direction: what if I thought bigger?
I decided to come up with a goal that was big enough and ambitious enough that it would take at least a decade to achieve. I decided that rather than selling assets in my 30s, I would focus on using leverage to buy up more assets.
In the words of The Alchemist, I came up with my Personal Legend:
I want to own 10+ businesses doing a total of $100 million or more in revenue in 10 years.
So, how did I reach that specific, ambitious goal? Let me share my journey:
After reflecting on the times in my life when I felt most fulfilled, I realized that:
So I knew my 10-year vision would need to afford me opportunities to continue learning and growing every year.
Paul Graham hints at the strength of curiosity and interest in his essay, How to do Great Work:
The work you choose needs to have three qualities: it has to be something you have a natural aptitude for, that you have a deep interest in, and that offers scope to do great work. - Paul Graham, Found of Y Combinator
This quote also hints at my next point…
I’ve always believed that I’ll achieve 100x more if I lean into my strengths rather than paper up my weaknesses.
I’m an activator with strong communication and organization skills.
Knowing this, my role should be setting a path and delegating work to more detail-oriented people. That sounds easy, but it’s hard to do without a specific vision in mind.
Good CEOs are good delegators, but if you take it up another level, investors are even better at putting key people in place and getting out of the way. As I reflect on the next 10 years, I know I need to learn to think more like an investor and less like a small business CEO.
Most people don’t like to set specific numbers or timelines to their goals because it means they might fail by not reaching them.
But, I started working with a coach last year, and one thing he kept pushing me to do was to define my vision in specific numbers. It’s uncomfortable because I might not hit these numbers, but I know that having them is valuable.
I think the best goals have numbers that are both scary (“how will I ever hit this?”) and exciting (“wouldn’t it be cool if I did this?”).
“When you want something, all the universe conspires in helping you to achieve it.” - The Alchemist
Belief is powerful, but it’s even more powerful when you can convince others to join you.
So, I started being open about what I wanted to do. Immediately, I attracted supporters who offered introductions, advice, leads, and partnerships.
I even found a partner who joined me and gave me the support I needed to make the first acquisition.
There’s a huge difference between having a big vision and making a concrete plan that gives you the first step toward realizing that vision.
So, I built a model, broken down by year, that showed me how quickly I’d have to move and the milestones I’d need to hit to make this happen.
Even if reality looks nothing like my model, the fact that there is a model makes the whole thing seem real. This model made my first step clear (buy another company) and it gave me the confidence to tell others that this really is possible.
In meeting hundreds of entrepreneurs with varying degrees of success, I’ve found the most successful and fun to talk to are the ones who have a big vision they’re after.
You might think building a 10-year vision would be limiting, but the opposite is true. Having a vision gives me clarity when making decisions while allowing me to be flexible about how I’ll actually achieve the long-term goal.
But, setting a big vision is still scary and hard.
If you’re struggling to define a big vision for your business or life, I’d love to hear how I can help. DM me on Twitter to continue the conversation.
]]>My team would come to me with all the hairy issues and ask my opinion, and I would gladly offer my sage wisdom as an experienced engineer and leader.
This worked fine for a while, but after a few months of having my team to come to me with every difficult decision, I realized that I had created a monster.
Nobody wanted to make tough calls. I had trained 5 intelligent, capable, independent engineers to bring every big decision to me before moving forward. Our velocity slowed to a crawl as I realized that I had made a huge mistake for the long-term health of my team.
I was struggling to keep up with all the questions and I felt like I couldn’t take a day off or the team would be completely immobilized. So, I worked longer, harder, and wrote more than I ever had before to make sure my team was constantly unblocked.
I can’t remember who finally told me this, but one of my mentors at the time was very straight with me:
“Why are you coming up with all the solutions? They’re smart, why don’t you make them bring you the answers?”
In hindsight, this seems so obvious. By always offering my opinion on every topic, I had given my team the impression that I knew it all, and since they naturally wanted to please me, they’d let me make all the tough calls for them. They looked good for bringing up issues, and I got to stroke my own ego by solving all the problems.
But, I had made a huge mistake for the long-run.
In the short-term, my choice to fix all the problems myself worked well. It ensured that we were consistent and unified in our approach, but it also came with a long-term cost. My team didn’t feel confident or empowered to bring solutions to the table. They were rewarded only for bringing problems up, and not for actually solving them.
The best teachers don’t give out free answers on the test. They give students the tools they need to find the right answers.
In the same way, the best managers delegate by giving their employees the tools and frameworks they need to answer their own questions.
One trick I’ve learned on this front is to never answer questions directly. For example, someone on my team recently asked me how they should respond to a client regarding a quality concern they had.
“I don’t know, that’s tough. How would you respond?” Was my answer.
Now, this employee gets a free shot to craft a response to me and explain their rationale. When they came back with a response, I immediately approved it and we moved on. I told them that they had a really good response and said that next time, they are free to just send it without my approval.
From now on, this employee is empowered to make decisions about client communication, and I’m now free from reviewing every email that goes back to a disgruntled client.
“Recently, I was asked if I was going to fire an employee who made a mistake that cost the company $600,000. No, I replied, I just spent $600,000 training him. Why would I want somebody to hire his experience?” – Thomas John Watson Sr., IBM
The other key part of effective delegation is allowing people to mess up.
Let’s say that the next time this employee responds to a client, they make the situation worse. Maybe they get confused and tell them the wrong thing, or they don’t fully address their issue.
Eventually, I’ll find out about the mistake, and now I have two options:
Option 1 dis-empowers the employee and puts me back in the decision-maker seat. This person is never going to respond to an email without my clearance again, and now I’m stuck reviewing emails all day instead of running my business.
Option 2 empowers the employee to figure out the root cause of the issue. It puts them in control of the situation and the possible solution. They can also suggest improvements to our process that might help others avoid making the same mistake, which would be a huge benefit to the company.
People learn the most in their careers from mistakes. How you as a leader respond to those mistakes shapes what your employees will take with them into the future.
Most entrepreneurs I know struggle with delegation. If you do or if you’ve figured out other tricks to help you do it better, I’d love to hear them. Send me your thoughts on Twitter.
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