I Started A $48K/Year Newsletter For Sneaker Heads

Hello! Who are you and what business did you start?

Hi - I’m Casey Woodard. I am the founder of KickFlips - the email newsletter and Discord community showing you exactly what sneakers and streetwear are available for you to make bank flipping for a profit.

Several days each week, sneaker retailers release limited-edition sneakers and streetwear that can be resold for exponentially more than the retail price. KickFlips sends emails every drop day, notifying subscribers of what and where sneakers are releasing and how they can maximize their profits.

The base version of KickFlips is completely free. There is also a paid “Pro” version that comes with additional exclusive drops, as well as resources to increase one’s odds of winning these profitable releases.

Since its inception, KickFlips has expanded into other profitable flips such as clothing, gaming consoles, graphics processing units, tickets, and more. While KickFlips is branded towards flipping sneakers, our members tend to make even more from these Pro exclusive flips, as they are higher-ticket items than many sneakers. The long-term goal is to become the premier free flipping resource for resellers.

I started building KickFlips in January of 2021 and launched in late February. Currently, KickFlips is bringing in about $4,000 a month in revenue with roughly $150 in expenses. In the 5 months of its life, KickFlips has grown to a little over 1,500 total users almost exclusively through word of mouth and referrals.


What's your backstory and how did you come up with the idea?

I got my first summer job at 11 years old working on a farm, and I HATED it. But I learned a valuable lesson: It’s better to get paid for your brains than your time.

If there’s a single tip I have for anyone looking to start or grow a business, it is to get involved in a community of successful entrepreneurs.

After that summer, I started looking for ways to make money that didn’t involve manual labor in a field during the summer heat. I discovered flipping items off Craigslist. Looking back, it was wild that my parents were ok with my 16-year-old brother driving me to meet strangers in parking lots to buy and sell things. But, after the first few profitable flips, I was hooked. I could make more in 30 minutes than I made in a full day on the farm. I started looking into other ways to make money flipping items and eventually stumbled onto sneakers.

Over the years, I’ve had countless friends ask me to show them how to make money flipping sneakers, video game consoles, GPUs, and more. I knew from a past business that if everybody inquires as to how you do something, then there is a market for your knowledge. I got so many people asking me to teach them, that it became crystal clear there was a large, untapped market for people who are interested in learning to flip sneakers.

Sneaker-reselling communities and resources already existed, but were all too expensive or ineffective. A $5 texting service didn’t offer any help to someone new to sneaker-flipping. A $99/month Discord group membership was far too rich for anybody who simply wanted to test the waters for the first time. There didn’t seem to be a decent free resource, so that was the logical market position to target.

Take us through the process of designing, prototyping, and manufacturing your first product.

The first step was to figure out the most effective medium to deliver this information. Texting is not a rich enough form of communication. Facebook groups and Slack channels require too much hands-on management. I needed something short and to-the-point, while still being able to send links and pictures to convey the specifics of each profitable sneaker release. Email is the best medium for what I was trying to convey. Eventually, I added a Discord channel for Pro members, which I believe was a huge value-add.

The beautiful thing about creating a digital product in 2021 is that there are a plethora of low-cost tools at your disposal. Creating a minimum viable product is not going to be a drain on any resources other than your time. Some entrepreneurial friends and I have created cool projects utilizing no-code tools and a little elbow grease. A Carrd website, a ConvertKit email template, and an adequate presence in the right subreddit can give you a decent kickstart literally for free. Thanks to these first two resources, I had a prototype running in less than 30 hours of work.

I was new to Carrd and their Pro plan allowed me to create up to 50 sites. In true entrepreneurial fashion, I figured that if I was going to practice web design, I may as well get paid for it. Thus, I reached out to a handful of local companies to redesign their website. That first week, I redesigned a local artist’s website for $1,000, which acted as the initial funding for KickFlips. KickFlips was truly the definition of a bootstrapped side-hustle, rather than the launch of a full-fledged business.

It’s better to get paid for your brains than your time.

The biggest prototype challenge was figuring out which features to include in the free version and which features to include in the Pro version. If you give too much value to the free group, then there’s insufficient incentive for your customers to upgrade. If you give too little, then they will assume that the paid version also can’t be that great and they’ll unsubscribe altogether. This is still a dance I’m figuring out, but it’s important to strike a good balance in that regard.


Describe the process of launching the business.

Looking back, my launch (if you can even call it that) left a lot to be desired. I built KickFlips in January of 2021 and gathered feedback from friends and family until the middle of February. However, my “launch” was really just me telling my friends and family to tell their friends and family, as well as covertly plugging KickFlips on Reddit and Facebook groups. There was no pre-launch email capture, no Facebook/Instagram ads, no big campaign, or anything remotely resembling an actual business. It was definitely an amateur show.

Despite my lackluster “launch”, the word-of-mouth snowball started growing slowly. After a month, I had already amassed a couple of hundred subscribers - 100% organically. More importantly, I had a very strong paid upgrade rate of well over 10%. In my eyes, this upgrade rate seemed to validate the business model I had chosen.

After all, 1,000 true fans is better than 10,000 passive customers.

My “big break” came 2-3 months after launching KickFlips. The founder of (in my opinion) the best retail arbitrage Discord group dm’ed me on Twitter saying that he was a KickFlips Pro member and a big fan. His group - Products For Profit - was growing rapidly and he wanted to expand beyond retail arbitrage and into sneakers, clothing, GPU’s, gaming consoles, and the like. We worked out a deal where I would essentially private label my KickFlips emails for his Discord group, with a mix of his groups’ and KickFlips’ branding. This resulted in a deal that will continue to grow as that group grows but is currently bringing in around $2,500-$3,000 per month.

In addition to that contract, the retail arbitrage leads from Products For Profit are top-notch and I would estimate that my affiliation with that group routinely makes me hundreds or even thousands each month because of those leads. I know others are making tens of thousands each month because of this group. I truly cannot say enough good things about Products For Profit, the people there, or the quality of their leads.


How are you doing today and what does the future look like?

Word-of-mouth has always been the best way for me to attract customers. I tried Facebook ads and saw user growth, but those subscribers rarely opened the emails and often canceled soon after joining. I purged the list of inactive users and decided - at least for now - to keep my ad spend to a minimum until I nail down my targeting.

A few months in, I reached out for advice to Noah Kagan - who I am grateful to call a KickFlips subscriber. His advice was: Make sure all your friends and family subscribe and make the product so good that, once they join, they can’t live without it. After that, growth will take care of itself.

I took this advice and ran with it. After all, 1,000 true fans is better than 10,000 passive customers. I’m sure I could have a higher subscriber count if I funneled more time and effort into paid ads, but the customers would be less engaged and also less likely to upgrade to Pro. My conviction is that if I keep improving the product, my customers will keep sharing the message.

From a retention standpoint, I’ve found that I regularly have to be in my customers’ faces about “Here’s what you missed not being in Pro”. At first, I was struggling to get many members to upgrade. I naively assumed the “If you want XYZ features, then join Pro” line in the free emails would sufficiently highlight the value offering of KickFlips Pro. That’s very much not the case. Ever since I started sending out regular emails showing members exactly how much money they missed out on that day or week by not being in Pro, the upgrade rate started increasing.

I’m a big believer that being a time billionaire is better than being a money billionaire.

In that vein, I had to be persistent with this call to upgrade. There have been so many times that someone has upgraded after 2-3 months of these regular “Here’s what you missed” emails - even though they had been opening them every single week. With a new company, customers are prone to not fully trust you until they’ve had some time with you. Don’t think that one single call to pay for your product is going to seal the deal. Stay in front of them.


How are you doing today and what does the future look like?

KickFlips turned profitable after about 2 months. I attribute this to the combination of low costs, and a strong paid upgrade rate. However, while my customer acquisition cost is essentially zero, the lack of paid advertising makes for a slower growth rate than I could potentially attain with ads.

I am currently at around 1,500 subscribers after 5 months and brought in revenue of roughly $4,000 this past month on about $150 in expenses. Maintenance for KickFlips requires around 20 minutes from me each day, with any additional time spent on the growth side. This could involve anything from social media management to planning growth and upgrade-oriented campaigns.

In that vein, I am still testing various advertising options, but have yet to successfully crack that code to a satisfactory degree. Success in this area seems to be the next step in getting KickFlips to the next level. In testing, my free member CAC has varied from $1-2, with my paid member CAC being roughly 10-15x that. However, the LTV of a member acquired through paid channels has been about 25% of one acquired organically - due to their shorter customer lifespan. Over the past few months, my ROAS has essentially been break-even. Thus, an increasing amount of my time on KickFlips is spent contemplating and testing both paid and non-paid growth strategies.

My goal is for KickFlips to be consistently making $5,000 in monthly profit by the end of 2021 and $10,000 in monthly profit by the end of 2022. More importantly, I want KickFlips to continue to consume less than 30 minutes of each day unless I choose to spend extra time on it. After all, KickFlips is still a side hustle as I work to grow a B2B business that is a bit more mature.

I have an incredible amount of respect for those who are grinding 100-hour weeks, trying to shoot the moon with huge ideas. But my goal has always been to make decent money and have complete freedom over my time. I’d rather make $10,000/month with 10 hours of work each week than $100,000/month with 100 hours of work each week. I’m a big believer that being a time billionaire is better than being a money billionaire.


“If you’re not embarrassed by the first version of your product, you’ve launched too late. - Silicon Valley”

What platform/tools do you use for your business?

Carrd - the easiest way to build a website. Wix and WordPress are far more flexible, but even an idiot like me can scrape together a halfway decent site on Carrd with no coding experience.

ConvertKit - one of many email newsletter tools. I chose Convertkit because the Pro version includes integration with Sparkloop.

Sparkloop - a referral tool that gives each user a traceable referral link so they can refer to their friends and get rewarded for each referral. If you run an email newsletter, make sure you are incentivizing your current subscribers to refer to their friends.

SimpleTexting - I use this as my texting service to notify Pro members of upcoming and last-minute drops. Texting is rather pricey, so I’ve moved over to Discord for a lot of messaging applications. However, SMS still has its use cases.

Discord - this is where I host my Pro member community. Discord is essentially an ultra-organized group message that also has intense customization options and custom-coding possibilities.

Teelaunch - the print-on-demand (POD) supplier I use to create the merchandise that gets sent to subscribers as a reward for referring other users. I started using Teelaunch when I launched a POD Etsy shop and I believe Teelaunch has the best combination of prices, fulfillment times, and customer service.

Canva - it’s basically Photoshop for dummies. I do graphic design for all of my businesses in Canva. It’s a drag-and-drop editor with pre-set templates and is highly intuitive. It may not be as powerful as photoshop, but it can get you 95% of the way there with 5% of the learning curve.

Gumroad - acts as my sales page and payment processor for the paid Pro members. You can use a processor that takes fewer fees, but Gumroad is the path of least resistance for a bootstrapped project in the digital product space.


What have been the most influential books, podcasts, or other resources?

Books -

  • The Snowball - Warren Buffett’s biography. So many lessons - the biggest of which is to play the long game.
  • The Psychology Of Money - This has more to do with personal finance than entrepreneurship, but there are fantastic lessons within - perhaps my favorite of which is the idea that having “enough” is not a dollar amount or destination, but a state of mind. Money matters, but your life today is more valuable than your bank account tomorrow.
  • The Subtle Art Of Not Giving A F*ck - Starting a business involves putting yourself and your work out there, taking chances, and looking like a failure or wannabe until long after you’re not. Caring about what other people think will do nothing but set you back. My default setting is to be a people-pleaser who wants to be who everyone wants him to be. I don’t want to step on toes, risk embarrassment, or deal with confrontation. Screw that. Your job is to disappoint as many people as it takes to avoid disappointing yourself.

Podcasts -

  • My First Million - The best podcast for entrepreneurs, without a doubt. Sam and Shaan discuss ideas, frameworks, and all things entrepreneurship, as well as interview big players who have started successful companies.
  • The Alpha M Podcast - My friend and I run a marketing company that works with several companies in the fitness and men’s fashion space. Aaron is one of the biggest names in men’s fashion and lifestyle, with over 6 million Youtube subscribers and several successful businesses. One of those is Pete and Pedro, which was featured on Starter Story in June. Aaron discusses his journey in starting several companies and interviews numerous entrepreneurs who have also started successful businesses. (Also, Aaron - if you’re reading this - let’s grab a coffee and talk marketing)

Next time you're considering putting off that cold email or skipping a workout, throw $200 on the line. Do you really want to spend $200 to not improve your business or health?

Advice for other entrepreneurs who want to get started or are just starting out?

Right now, pull out your phone, set the timer to 60 minutes, and work on your idea without a moment spent brainstorming or strategizing. Just start building something. What you make in these 60 minutes will unequivocally suck, but it will be better than what you had an hour ago. I can’t begin to count the number of people who tell me they have an idea but never end up getting past the daydreaming stage.

A common saying in Silicon Valley is “If you’re not embarrassed by the first version of your product, you’ve launched too late.” In the self-improvement world, it’s “If you’re not embarrassed by who you were 6 months ago, you’re doing it wrong.” Perfectionism has no place in entrepreneurship. What you call “planning and strategizing”, entrepreneurs call “procrastinating”. In the words of General George Patton, “A good plan violently executed now is better than a perfect plan executed next week.”

Also, there’s a lot of unjustified hate on 9-5 jobs nowadays. If you have a business idea, your 9-5 is the VC fund for your business. 90% of the time, you don’t need to quit your job to pursue your business until you actually start to gain traction. It’s a lot easier to play the long game when you don’t need to take shortcuts to buy groceries and pay rent.

Third, put your money where your mouth is. My friends and I have a process in place: Whenever we need to do something but don’t want to, we Venmo the other guys $100 each. If we don’t get that task done by a hard deadline, the other guys keep the money. No refunds. No excuses. You need to manufacture pressure and incentives to do the things you don’t want to do. Next time you're considering putting off that cold email or skipping a workout, throw $200 on the line. Do you really want to spend $200 to not improve your business or health? Didn’t think so.

Finally, I don’t believe there’s any such thing as a self-made man - not that I’ve remotely “made it”. I’m incredibly fortunate to have made friends with entrepreneurs who are far more successful than myself. We are always bouncing ideas, problems, and strategies off each other to help our friends grow. If there’s a single tip I have for anyone looking to start or grow a business, it is to get involved in a community of successful entrepreneurs. Find them in your city, DM your idols on Twitter or start an entrepreneurship Facebook group. Do whatever it takes to get plugged in with people who already do what you want to.

Are you looking to hire for certain positions right now?

I just hired my first employee ever, which is an incredibly exciting, but also weird, feeling for a 23-year old. They are part-time and handle most of the graphic design, social media, and clerical work for KickFlips. I could see myself looking for an operator in the future, should I ever decide to make KickFlips 100% passive for me. However, I am not hiring for any positions at the moment.

Where can we go to learn more?

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