Timing in Entrepreneurship

Timing is the most important aspect of business. If you have the right timing you can have a terrible product, terrible service and barely be good at business… and you’ll still win.

It’s much like Online Entrepreneurs who first started a business since 2018 and until this year and thought everything they touched turned to gold. Was it that they were good, or did we just see the largest credit expansion and bull market in recent history (or ever)? 🙂 

If you don’t remember who I am, I’m Scott Oldford. I mentor, advise and invest in Online Businesses. I write this newsletter for Entrepreneurs who enjoy acquiring, building, buying and selling businesses and give you an inside look at my portfolio of internet-based businesses.

In essence, timing rules all in the landing of business and the problem?

If you’re too early, you’ll miss the party and potentially run out of capital to sustain the return.

If you’re too late, you’ll have nearly no unfair advantage and not be able to profit.

In both cases— it will make it impossible to succeed.

The problem, on top of this? Visionaries are almost too early and those who follow trends are almost too late.

In essence, I’ve found that the people that are luckiest on timing are those who actually didn’t even think about timing at all— they simply stumbled into it.

This causes a bit of a problem, if your investment strategy is based on ensuring you have the right timing.

While, I’ve never had the issue of being too late— ever. I have been too early multiple times and I know the pain that occurs when you can’t keep your early position.

The first time this happened was when I was still a teenager. I was working on an advertising technology and used almost all my money to fund the development and expansion.

In the end it didn’t work and to this day, the technology has yet to be widespread. However, someday when autonomous cars are fully integrated into society— I expect it’ll be the “next big thing”.

I’ll be 30 years too early on that one, by the time that happened. However, that mistake on timing? It caused me to go in over $1M in debt because I deluded myself by the timing and thinking I could withstand the timing.

Thing is… I wasn’t VC-funded and I could out-spend myself in market share or the understanding of a market with that business.

I shut it down and it was one of the most painful experiences of my life— including asking my Mother to remortgage her home for me.

In building a portfolio and being an investor— I very much have the same issue.

My bets, if they work should have incredible upside and if they don’t, they should have limited downside.

As I wrote about earlier, while I was raising capital for my portfolio, I decided to abandon that strategy and go with profitability by Q4 2023, instead of our expected breakeven by Q4 2024— an entire year early.

That is a post for a different day— however, that strategy of changing from growth with raised capital (and my own) versus allowing the portfolio to become profitable and use it’s own capital for it’s expansion— was a choice based on what I’ve learnt about the “right” timing.

See… while a large part of the portfolio aren’t massive bets into the future— they do require “waiting” for the future.

Properties such as sponsorships.com, will take multiple years to be where they need to be and they will require regular advertising to be less effective. This will happen in time, however, that day hasn’t occurred.

Other properties such as onlinebusinessowner.com simply take time because they are based on being a brand versus a personal brand, which means it takes longer to connect with an audience.

Other investments such as cohere.live require that coaches realize they don’t need to spend $50K on a custom funnel or investments like roezan.com allow for someone to realize they should use SMS, but not like they think they should.

Or for example, in our minority ownership of https://emailsmart.com we know that there is no amount of money we can spend to show people the importance of email deliverability. We simply have to wait for the major players like Google to inform our potential customers— and when that occurs, it’ll be an automatic gold rush.

In every single case of our 40+ businesses and investments— timing is everything and when it comes to timing you have a few options for the waiting period.

#1. Spend money to inform your audience.

#2. Actively Wait

#3. Passively Wait

In the first, it’s most using your marketing as education to help people to come into your “fast lane”. It can be an uphill battle and the difficult part is that someone can easily come and steal your customer afterwards, while you spent all the money to inform them.

In the second, it’s about building the infrastructure of the business and getting ready for the market to be ready, however, majority of your money isn’t spend on marketing and sales, but rather, being “ready”.

In the third, it’s about understanding where the market is going and dipping your toes in so that when it becomes warm, you can go in that direction.

When we were planning to raise money, I had our portfolio mostly setup for #1. However, I’ve had to revert to #2 and #3 in not raising money, allowing for our “bets” that don’t require future-timing to take front and centre.

What this meant is that I had to restructure parts of the business and things that were bets that were long-term.

A few examples:

For Sponsorships.com, it meant slowing the non-educational elements of the business and decreasing the amount we were spending by 75% per month.

In the case of Wisdom Media, our newsletter side of the business, it meant selling 7 of our newsletters, focusing on what we had and focusing on a single form of monetization and restructuring the way we managed it and will grow it in the future.

In many places in our portfolio, we had to focus the “here and now”, versus the 2026+ future due to one simple element.

Your amount of capital, allows you to decide how much you play into the future.

For some of our businesses, we picked the passive, waiting for the timing to bring it back to the spot light.

For some of our businesses, we picked active, simply decreasing our marketing and sales.

And for a select few, we’re still “all in” because we know that the timing is “right now”.

The problem is… trying make a call on timing, is difficult. Even in not taking more capital, it was a difficult choice.

In the end, for me, it came to principle. The investors that were committed didn’t work out and I’m unwilling to take capital from anyone who I don’t resonate with deeply and are strategic. I felt that the direction of the future, needed to be based on “here and now” profitability, versus my intention of profitability in late 2024 and early 2025.

Is that painful? Yes. Very, very, very painful.

However, what I’ve learnt about timing is that it’s far more painful to go blindly in the delusion that you’re on time. Then it is to realize that perhaps the compass is a little off and you need to realign.

Doing this for a single business, would be easy. Doing it for an entire group of businesses? A challenge.

The lesson for today?

Timing is the most critical thing you must think about every single week as an Entrepreneur.

It’s important to understand which stage you’re in. Further, each part of your business has these stages. Everything from your team to traffic sources, to offers.

Everything has “perfect” timing and the more you’re intentional about the timing, the better choices you can make.

Why?

Well… Almost every entrepreneur I’ve ever met made the right choices. However, majority of them, made the right choices, in the wrong order.

And the right choices, require the right order, 100% of the time.

- Scott

P.S. I’m proud to report that our P&L is now completely profitable and we switched from our strategy of burn-to-scale-and-grow to profitablity in less than 45 days. It’s been painful and while I would rather not do it, it is the best option and every business requires expansion and contraction for success 🙂