Let’s start with the big win for 2023…

At the start of the year my company InboxDone.com finally surpassed the benchmark $83,333/month in revenue. This is the number that means your company is a ‘7-figure business‘ because you’re doing a million a year in revenue.

We’re doing $100,000+ months now, which on some level is incredible to me because I remember 20 years ago struggling to reach a six-figure YEAR as a new entrepreneur.

People love to talk about 7-figure businesses, especially if you’re a coach of anything to do with business. For me, since I don’t really coach so much anymore (this was the first year in a LONG time that I had no coaching programs for sale), it wasn’t important for my social proof as a coach, but it sure was satisfying to hit that number as a founder.

My original expectation was to hit this number in about half the time it has taken to get here. While that contributed to frustration and lack of commitment (see below), it surprisingly has made me value the achievement far more than I expected now that we are there. I guess the journey to get here makes you appreciate it more.

To be completely transparent, just because your company makes a million dollars a year does not mean you are keeping all that money.

InboxDone has a team of 50+ staff, plus I am a 50% shareholder with my co-founder. After all the expenses are taken out, my monthly income from the company is on par with what I used to make with my coaching business when it was generating $300,000 a year.

My coaching company had FAR fewer people involved and thus far less expenses. I could keep as much as 80% of my revenue as cash I could draw out of the company (then pay hefty taxes).

On the other hand, InboxDone as a company can be sold, where my coaching business was very unlikely to find a buyer since it was so tied up with my personal brand.

It goes to show how different business models can be. When you decide to start a company, the business model you choose is a huge decision — one you should consider carefully.

With InboxDone we’re well on our way to the next milestone, a ‘multiple 7-figure a year business’, but let’s stop talking about money for a moment…

I Was Scattered This Year

Throughout my career as an entrepreneur I’ve always been good at knowing what is ‘the thing‘ I have to do.

There’s usually one task or set of tasks that drive forward the main money making project that pays my bills each month. It might not be growing as fast as I like, or maybe I don’t feel 100% committed to the business, but there is an action or a set of actions that I know if I keep doing, good things happen — growth happens.

My first company in the early 2000s, BetterEdit.com, an essay and thesis editing agency, was never a passion for me, but it did work and made the money I needed for rent and food. I knew that as long as I put up posters on university campuses and created content and backlinks for SEO, I’d get customers.

I maintained those core activities, but a lot of the rest of the time I did other things — launched websites that went nowhere, read about completely different business ideas, felt insanely jealous of what other entrepreneurs were doing, and so on. I was honestly a bit of a mess, but it was my early twenties, so understandable.

Fast forward a few years and I’d gone and stumbled my way into a coaching and teaching business, with a blog and email newsletter as the engine driving it.

For more than a decade I made sure that I continued to write blog posts and email newsletters (I still do to this day, just not as consistently as I did back then). I knew those two activities gave me the platform to generate sales of whatever I was selling.

For the last few years I’ve remained committed to improving the core marketing engine for InboxDone. I’ve made sure to never neglect that engine, even when I used a lot of the rest of my time for other things.

This year I continued to pour money and time into my software side project Candid.is. I briefly started working on second agency for AI services, then stopped. I bought domain names I shouldn’t have… and so on.

I could dive into a discussion of the psychology behind why I deliberately distracted myself, but really it’s a simple answer — commitment, or lack thereof.

When you’re not sure your company is the company you want to focus on, you look for something else. There are many elements at play — speed of growth, what you find creatively compelling, income goals, business model advantages/disadvantages, a desire to ‘expand your empire’ into multiple businesses, enjoyment of the actions you currently do for your current business — all these things play a part.

I can report back that I eventually came to my senses in the final quarter of 2023 and followed the advice I’ve so very often given to others — you have to FOCUS.

I made the choice to commit to the one thing that was actually working, my company InboxDone.com. No side projects, no new companies, no throwing money at something you can’t really invest the time and mental attention to make it work.

I still find myself having thoughts about ‘new things’ (every entrepreneur does), but I have this little voice in my head that slaps me back with a “NO!” very quickly, at least no for now.

One thing I practice that helps me gain clarity on what I really want to do is this thought experiment. I ask myself…

Would I want to do the things or be in the situation that I know I would be in if I decided to ‘open the door’ to that new idea?

This is especially helpful when I think about getting back into the personal brand content and coaching game. This is the most common idea I have since I know the business model so well and I enjoy teaching and selling information products.

It’s hard not to want to teach and share what you’re learning as you grow a business, and get paid well for it. This is especially true when in a previous business you did just that, earning millions of dollars and enjoying the exposure and attention that comes from being a content creator.

When you know how to do something, it’s easy to think you can successfully walk down that path again.

When I did this thought experiment, I quickly come to terms that I don’t actually want to be back on the ‘content treadmill’, or be out there oversharing every thought that comes to me. Nor do I want to start from almost ground zero with a brand new product, with so many basic things to do and create just to give myself a chance of success (testing landing pages, webinars, sales videos, launches, ad campaigns, etc).

In truth, what I want to do and the situation I want to be in, is exactly where I am at. I get to focus on being the co-founder and CMO of a 7-figure company that solves a real need, has systems and amazing people delivering value to our clients, and I’ve already spent years building up ‘assets’ that we get to leverage today.

My job is straight forward — I run marketing experiments and work with a small marketing and sales team in order to bring in new customers. I still get to learn new skills, create content, but it’s not about my personal brand and it’s very, very linear.

Our value proposition is not complicated, so selling it is not complicated.

Best of all, people value the service and thus we change lives. It’s amazing to sell something that truly represents why I became an entrepreneur — FREEDOM. InboxDone sells freedom, or at least a way to get back time and mental space, which you are free to use as you want to.

This is why I finally made the choice to not just do the core things I need to do for the project that pays my bills, I decided to make this project, this company (InboxDone.com), the only thing I do.

I decided to focus and keep making something that’s great even better.

What Happened With Candid?

What I went through this year with my software project Candid demonstrates how eventually, the decision to focus can’t be avoided, if you want something to succeed.

The first iteration of my concept for this business came to me over three years ago. It then changed, changed some more, and more (you get the idea), and then finally I settled on something that I started building with a Ukrainian software dev team.

Throughout 2022 and much of 2023 I guided my designer and coders to create Candid. It was fun, a side project where I got to be entrepreneurial and creative, giving feedback and requesting changes, but then let the team do the work to build it.

It cost me quite a bit of money, so much so that I almost raised outside investment, but eventually decided to give myself a cap of cash to spend each month.

It felt like an expensive hobby, where I could learn about getting a software project to market without blowing my life savings. This obviously slowed things down, so not ideal in the fast-paced world of software startups, but I knew I couldn’t go all-in financially or mentally, at least not yet.

I had dreams of Candid taking off, but I wasn’t expecting that to just happen instantly (I think all entrepreneurs dream of building a ‘rocket ship’ that just explodes in growth from word of mouth).

I knew at some point I’d have to switch on some kind of marketing to get users, get feedback, hopefully generate some revenue, and grow from there. That wasn’t going to happen until I had at least a working beta version of my software.

Eventually, 18 months later, the day came when I had that working version of Candid (around August of this year). I’d also had my tech team build a website and spent quite a bit of my personal time writing articles for it. I had what I needed to go to market and start telling people Candid exists.

I did this using my lowest hanging fruit options first. I told friends, sent an email to my newsletter and shared posts on social media. The net result of this was not much. I was disappointed, but not surprised. I knew there was so much more I could do to create awareness… but that was the problem.

I now faced a decision point. I had a company already making money that I was in charge of growth. I had a software startup that needed marketing just to prove if it could be a viable business. Each moment of marketing energy spent on one company was not spent on the other.

It was easy to have Candid be a side project while it was in development. I’m no coder, so the dev team were busy while I was mostly working on sales and marketing for InboxDone.

Once Candid was ready, then it was my turn as the growth guy to get the word out. That meant a conflict in how to use my time — split it, or focus on one project.

In the end the decision was straightforward. The smart choice, and the one I felt more confident in returning income, was to grow what was working into something bigger and not start from scratch with something that may not work at all.

I had to put Candid on pause, and go all-in on InboxDone.

It’s worth noting this decision became easier over time because InboxDone continued to grow all the while I was building Candid.

At the point I started Candid, InboxDone was smaller and not exactly consistent. If you asked me at the start of Candid two years ago to choose between InboxDone and the new project I may well have selected Candid because I’d already spent 4 years on InboxDone, with not much personal income returned to me for all the effort put in (I chose not to take any salary for a couple of years so we could use what profit we had for marketing).

I don’t consider Candid a dead project, but I also feel good about having just one thing to focus on. If I exit InboxDone, I will seriously consider re-focusing back on Candid. That decision will depend a lot on the situation I am in at that time.

I’m quite proud of what Candid is even now, despite having no users. It does something I believe is useful. I know how hard it is with software to get just to the point where you have a working tool.

If I can attract a first cohort of users who find the platform beneficial, then I think it could take off. For now that question will have to remain unanswered.

I Learned How To Market Across New Channels

For most of my career as an entrepreneur I’ve been a content marketer.

That means I’ve primarily used things like articles and podcasts and email sequences to sell my products.

I’m pretty good at telling stories and making sales using proven psychological frameworks that drive action (social proof, scarcity, authority, authenticity, etc).

For so very long, most of my new customers came from Google. I had a blog that ranked well that fed people into my newsletter, which I could keep going back to when it came time to sell my programs.

It is a beautiful system, that was mostly free, besides the time and effort required to create all that content (no small job, but highly satisfying work!).

These skills and my existing audience came in handy to launch InboxDone, but I quickly found out they could only take us so far.

To put it simply, what had worked for me to acquire customers in the past, was not going to be enough for my new company.

This forced me to dip my toes into new marketing methods, albeit with a very small budget to start with.

You can read a list of the many marketing techniques I’ve implemented over the years, some that worked, some that didn’t.

While far from an expert, I now feel a lot more confident in using Google paid ads, LinkedIn paid ads and LinkedIn cold outreach to attract customers. I was already familiar with podcast marketing, but InboxDone is the first company where we also did a paid sponsorship on a podcast – Jenny Blake – that had proven effective after I first appeared as a guest (we had a podcast guest campaign running for a number of years as well).

None of these channels have become significant breakthroughs for growth, but each one, along with Google organic search, word of mouth, and my own personal brand from my blogging and email marketing days, continue to bring in customers.

If you look at November 2023, InboxDone had 9 new customers sign up, coming from Google paid ads and organic search, LinkedIn paid ads, podcast referral, existing client referral, and someone who knew me from my blog and email newsletter.

Having a number of marketing channels all working to bring in customers, all of which I started myself at some point, feels satisfying and also more stable. None of these channels work all of the time, but something is bound to work each month, with everything (or at least one or two channels) getting incrementally better over time.

I have many more marketing experiments I’d like to run, but with a limited budget there is only so much we can test. Most of the budget goes to what is already working, and we prefer to expand what already works (for example adding more to the Google ads budget if it’s performing well), rather than throw money at new channels that may return nothing.

I still get a kick out of learning how each new discovery call person found us. There’s something empowering about knowing what you are doing to reach people and attract paying customers is actually working.

I heard someone on a podcast recently say (I’m paraphrasing here):

First time entrepreneurs focus on product, second time entrepreneurs focus on distribution.

While both product/service and distribution are important, you do realize that to really push towards seven, eight and even nine figure outcomes, distribution becomes far more important than product. This assumes you have a product or service that is valuable (it already ‘fits’ a market need), so you know people will pay for it.

I mentioned earlier that one of the reasons I made the choice to focus on InboxDone is because we have ‘assets’ built up now.

These assets include marketing resources like case study/review interviews from InboxDone clients, which are great for paid advertising campaigns. Having a well-fleshed out website homepage, key articles that rank organically in Google, a hero video, and even an email newsletter sequence (at last!) – are all points of contact that help bring in customers, but take quite a while to build up.

One final thing I’ll mention about marketing this year… I feel far more capable to launch any new company in the future because I don’t have to rely just on content marketing.

Content marketing is great, but it’s slow.

It’s hard to test an idea if you rely on blog posts ranking in Google to feed some kind of email funnel.

Knowing enough myself that I can go direct with paid ads, cold outreach on LinkedIn, podcast sponsorship, plus my old bread and butter with content marketing, gives me options, many of which are quick to show an indication something is working or not.

I Remained Financially Conservative

As I wrote about in my 2022 year end recap, because of a combination of events, from SPACs crashing, the war in Ukraine, bad luck/timing with getting forms back from the Canadian govt, and being dumb chasing after reddit stocks, I felt very conservative in terms of how I was going to invest my money going forward in 2023.

The war in Ukraine continues, and although my solar farm in the country still exists, no money can go back to me overseas as there is a block on any funds leaving the country.

If — and this is a BIG IF — Ukraine survives the invasion and things reach a ceasefire, or some kind of ‘stable’ stalemate, or Ukraine somehow manages to eject the Russians or they leave of their own accord, then money may again be allowed to leave the country. If that happens, from 2025 onwards I’ll have a lot of capital coming back to me.

The only new thing I did in 2022 was to invest in high-dividend yield ETF stocks, which after monitoring for a while I decided to exit out of this year. I found the stocks would go down in value just as much as the dividends returned. This may not be the case long term, but I also wasn’t sure if housing my long term capital in this kind of investment made sense. I didn’t have a clear strategy for the future.

Infinite Banking/Whole Life Insurance

My long term investment strategy became more clear in 2023 when I discovered a new form of investing that is often used by the wealthy.

It’s called ‘Infinite Banking’ and applies a dividend-paying whole life insurance policy as a sort of personal bank for savings and loans.


Yeah, that was my reaction too when I first heard of it. I was SO CONFUSED. I became even more confused the more I initially learned about it.

My friend Andrew Murdoch from YT Era was my first introduction to Infinite Banking, which he had studied from the creator of the concept, an economist named Nelson Nash. Andrew did his best to teach me what he could, and I also got Nelson’s book ‘Becoming Your Own Banker: Unlock the Infinite Banking Concept‘.

I still didn’t quite get it, so I headed to YouTube and found this helpful deep dive course into whole life insurance from an insurance broker named Ryan Griggs. Ryan’s free course is over seven hours long, dry at points, but wow is it helpful to understand the practicalities of this kind of insurance.

I still had gaps in my knowledge, and since I’m a Canadian, I had to find out how Canadian whole life insurance policies differed from American.

As sometimes happens, once you became aware of something new, in this case using a kind of insurance for investing, I started to hear about it more and more.

Neil Patel mentioned he puts $300,000 a year into his whole life insurance policy on the My First Million podcast. Kris Krohn in his book ‘Have It All‘, includes an early chapter specifically talking about a kind of ‘savings account’ that the rich use — yes, a whole life insurance policy.

Kris Krohn delivered a really simple phrase in his book that finally locked in the main reason to use a whole life insurance policy — it gives you ‘double use’ of your money.

I say this made sense to me, but that was after studying all the other resources. There’s a lot more to it, and it won’t make sense to you if this is the first time hearing about Infinite Banking or whole life insurance policies.

I won’t go deep into it, but putting it as simply as I can, here is why I got a dividend-paying whole life insurance policy in 2023:

+ Tax Free Savings: The money you put into your policy earn dividends each year, which are tax free because you earn them as a return on premium, not as interest in a bank account or dividends on a stock (there are caveats to this, but let’s keep things simple). While there are no guarantees of future dividends, the mutual companies that provide these policies have a VERY long history of delivering dividends every year.

You’re probably wondering, how much are the dividends? This changes each year, but as a sample, since 2010 the company I took a policy from has paid out between 5% and 7% per year. Given the tax free nature of the return, you’re keeping as much as 25%-50% extra (depending on your tax rate) that you would have to give to the government in taxes. If your dividends are 7%, if that was another form of savings or investment, you’d be only keeping 5.25% or less after tax.

+ Double use of your money: The money in your policy keeps growing as dividends are returned and you pay your premiums (you can also add additional premium payments). That’s your savings account. However, you can also borrow against your policy, using that money to buy assets, without reducing your policy value and thus your dividend return. So you get the benefit of tax-free dividends on your savings and a large amount of your cash (capital) in the policy can still be accessed (hence, double-use).

As an example of this, in a couple of years my property loans are due for renewal. I intend to have enough cash built up in my insurance policy that I will get a policy loan and pay out 100% of what is left in one of my home loans from the bank.

The rental income from this property will continue to go towards paying back the loan + interest, but to my insurance policy on terms I control, not the bank, and since the interest goes to the insurance fund, which I am actually part owner with my policy (mutual company), it’s contributing to the dividend return I receive and not bank profits.

+ Long term passive and retirement income: Assuming you continue to pay your premium, around the seven year mark (depending on rate of return) something magical happens — your dividends become large enough to cover the premium.

This means your insurance policy can ‘pay for itself’, if you choose to use the dividend to pay the premium. Take this further forward in time and your dividends will exceed the premium cost, so it will compound and ‘grow profits’ for you without you putting in any more money (compound passive income, if you stick to it long enough, and live long enough!).

Many people who have a whole life insurance policy, as they get older, use it like a retirement fund. They do this by taking dividends out in cash or getting loans against the policy that they never intend to pay back. The policy itself has enough value that it will pay back the loans at the time of your death, along with the death benefit from the insurance that goes to your beneficiaries.

All of this sounds confusing, and this is with me trying to simplify it! You can see why it took me several months of studying various resources before I decided this was a good strategy for me.

Note it made sense for me too because I have cash available and liquid investments I can move into my insurance policy over time. In the years ahead I may need to liquidate stocks or crypto to pay my premium or I could use profits from my business if they are there at the time.

It’s hard to predict the future, but I felt comfortable that I could get to the seven year mark (the point where my premium should be covered by dividends) based on the premium I planned to put into the policy each year, even without relying on business income. Of course you can always adjust your premium if you have to, nothing is locked in stone.

You DEFINITELY need to study and get financial advice to make sure this kind of strategy financially makes sense for you. Your current situation in terms of cash flow, assets, liabilities, all play a part in how you structure a whole life insurance policy. Don’t forget, it’s also an insurance policy and will pay a death benefit when you die. This may be the biggest benefit for you.

If you want to learn more about dividend-paying whole life insurance policies, this blog post has a good overview.

I should also mention that proponents of Infinite Banking consider this strategy more than just about having an investment vehicle.

It’s about taking control, leaving the traditional banking system and to some extent even leaving the tax system. It’s a libertarian way of thinking, to help you ‘break out of the system’ and have a tool that can in some ways function as a bank you control.

At first I found this way of presenting Infinite Banking confusing. It’s fun to hear about these ‘big ideas’ and ideologies, but if you can’t grasp the nuts and bolts of a dividend-paying whole life insurance policy, you shouldn’t jump in. I can see why Nelson Nash and his followers present this information, but I do wonder if it can be a detriment if that’s your starting point.

Other Investments

Besides adding whole life insurance and stopping high yield dividend investing, I didn’t make major changes to my investments in 2023.

I did grab pro-rata in a few of my most promising angel investments to maintain my equity when these companies raised follow-up rounds.

Due to economic conditions many of the startups I invested in are seeing negative or flat growth at the moment. They are also trying to avoid raising funds when capital markets are not appealing, so they are cutting costs in an attempt to extend runway with the cash they already have.

I have no returns from angel investing so far, so I can’t say this has been a smart investing strategy. It’s obviously high risk.

I did my first investment in 2017, and since companies tend to have an exit event somewhere in their 7th to 10th year, I may start seeing this from 2024 onwards. I don’t really expect it until 2025, as we need to move past the economic downturn and higher interest rate environment of 2023.

As I type this in December of 2023, the stock market and crypto currency prices are on the move up. For the last three months things have very much been turning a corner, so we may be looking at a recovery and bull market settling in again, or maybe not. As always, inflation, interest rates and global events play a big part in what 2024 will look like.

I’m happy to see all my crypto investments back in the green by some margin. Considering they were more than 50% in the red in the past two years, that’s a big turnaround (from -50% to +30% on Bitcoin in just a couple of months!). Those who have gambled with crypto are used to it — whether that’s a good thing or not is up to your tolerance for risk!

2024 Plans

Next year I plan to continue how this year ended. I am all-in on InboxDone as my main business focus. We had a very well known-client sign up at the end of 2023, and if that goes well, it could really help increase our exposure, so fingers crossed for that in 2024.

I’m also remaining conservative when it comes to new investments. The only way this changes is if there’s a ‘win’ with my current investments. A win could come back from an angel investment exit (if it’s a big one) or something changes in Ukraine (which honestly I hope for the best first for the country and my friends there, not just for my own financial benefit). I don’t expect either of these things to happen, maybe in 2025 — but who knows!

The one thing that is changing for me is where I live. I’m leaving Montreal, which has been my main home for the last four years. I’m presently finishing up converting my home into an AirBNB rental and then heading back over to Vancouver from January onwards. I will likely continue to travel, but use Vancouver as my main home so I can build up friendships and connections there.

Here’s to a great 2024!