The Big Five-Oh

Good Morning. Really quick... can you reply with your favorite song? I’m about to quarantine in my basement for the next week and I need some new music to get me through. Spotify/Apple Music links are preferred :)

If you’re receiving this email but haven’t subscribed yet, get in on the fun here. I want to hear your favorite songs too.

6️⃣ Months Later

Over the last (almost) six months, I’ve written two editions of Crashing Up per week. Throughout this time, I’ve spent countless hours experimenting and learning about what makes a newsletter successful. Fifty editions later, I’ve started to pick up on a few things. Today, I’ll be sharing my takeaways as well as a few adjustments I’ll be making go forward.

1. The Two Pillars

The foundation of a successful newsletter consists of two pillars: content and growth. No amount of marketing can help push shitty product, but if you have valuable content (which I think I do), it’s important to designate enough time and effort to spreading the word. This is where I feel I’ve been lacking, so I will be adjusting my writing schedule to allow for more marketing time. In order to efficiently and effectively promote your work, you need to know your target audience.

2. Find Your Niche

I initially started Crashing Up as a way to exercise my creativity and build a habit of writing consistently. I had no growth goals or topic direction, instead choosing to write about whatever interested me (many, many things). It so happened that much of my writing has centered around entrepreneurship, tech, and digital media. I quickly learned that in order to grow a successful newsletter (or business in general), you need to determine the following:

  • Who is my audience? (x)

  • What value does my product or service (in this case, my writing) offer to them? (y)

You should be able to describe this simply as:

  • I help [x] do [y]

In the case of Crashing Up, I’ve reformatted this to:

  • I write about how [x] can do [y]

Until now, I couldn’t answer these questions in a paragraph, let alone a sentence. Since I couldn’t define my audience, I had significant trouble identifying the right marketing strategy to reach them. I was all over the map. After much thought, here’s my new description:

I write about how entrepreneurs and creators can use technology to start, scale, and market their businesses.

While you shouldn’t expect much of the content to change in the future, everything I write or publish will be written through the lens of helping entrepreneurs.

Note: In my opinion, you can still be an entrepreneur without starting a business. Authors, YouTubers, and other content creators are all examples of entrepreneurs. This newsletter is just as much for them as it is your traditional business owner.

3. Be Unique and Insightful

I’ve noticed a common theme across my best performing emails: They shared my unique ideas and perspective, rather than summarizing current events or someone else’s ideas. The best engagement (shares, clicks, and replies) came when I offered readers actionable advice or new tools to help them in their day-to-day lives.

While all interaction is important, shares are the most telling sign of a well-written piece. They are the key to a self-sustaining growth flywheel, since your customers are doing the marketing for you.

There are two reasons why Word of Mouth marketing (WoM) is essential for building a business:

  • It’s free

  • It’s genuine

It’s one thing for me to tell you how great I think my work is, but it’s another to hear it from a reader or customer. Establishing this social proof, through shares or testimonials, is a great way to increase your visibility and fast track your growth. In order for this to work, you need to create content worth sharing. A great way to do this is to bring new thoughts or perspectives to an existing discussion or create an entirely new dialogue around your own ideas.

If Crashing Up has brought you value so far, I’d really appreciate either a share or a testimonial for me to use for my website. You can reply to this email or DM me on Twitter.

Share Crashing Up

Taking into account all of the above, I’ve decided to make a few slight adjustments to my existing newsletter format:


  • One unique and insightful long form idea

  • A podcast style interview with a guest entrepreneur, investor, or creator. This will no longer be named Friday Features (since…you get it) and will be also uploaded as a standalone podcast on streaming services like Spotify, Apple and more. New name is still TBD, so if you have a suggestion I’d love to hear it!

  • Tool of the Week


  • Friday Fuel will remain as is (a collection of links I’ve been learning from or enjoying recently)

Most importantly, I want to say thank you for all of the support and feedback you’ve provided over the last fifty editions. This is only the beginning. I’ve loved chatting with those of you who’ve reached out or replied to the emails and if you haven’t, I encourage you to do so. It’s my favorite part of this whole process.

🧰Tool of the Week

Bitcoin is booming, once again. At the time I am writing this newsletter, one bitcoin is worth $18,640, only $1000 off from its 2017 high of $19,783. Not too shabby given its steep decline in 2018.

With the holiday season approaching and the resurgence of the crypto craze in full force, a little Bitcoin chatter might find its way into your Zoom festivities.

If you aren’t familiar with Bitcoin or just need a refresher, you can use this article to catch you up to speed.

There are three ways to obtain Bitcoin. You can buy it, you can mine it (unless you enjoy spending a lot of money to set up warehouses of super computers, you’ll stay away from this one), or you can earn it. Today’s tool will help you with the last.

Lolli is a rewards browser extension that gives you Bitcoin when you shop online. The premise is simple. Shop your favorite Lolli partner brands (over 500+ well-known brands) and receive a percentage of your purchase back in Bitcoin.

Here are a few of Lolli’s partners:

If you like free money, sign up here. It’s a no brainer.

That’s it for this week. I’ve decided to give you some time to recover from your T(of)urkey comas, so I won’t be sending out an edition of Friday Fuel this week. I’ll be back to normally scheduled programming in the new format on Monday.

If you’re new here and want to catch up on some old editions, here are a couple of my favorites: Shovels in a Gold Rush and The SMS ComebackYou can also follow me on Twitter or check out for more writing.

Thanks for reading,