Why I built knoware

Why I Built Knoware

Like many people, I didn’t really have a handle on my finances. I had a few accounts, investments, a house, a mortgage, cars, debt. I had a general feeling that things were probably fine, but I didn’t really know.

And for a long time, that was good enough. Well, not good. I’m sure I had waste and plenty I could have done better. But the "ostrich with its head in the sand" method was basically my financial strategy.

After all, I was busy building a company. Heads down, putting out one fire after another and obsessively focused on whatever problem was directly in front of me. It gave me all the distraction I needed to never really take my finances seriously.

Then I sold it.

After more than a decade of building, suddenly the distraction was gone and the financial questions got louder.

• Was I actually in good shape?
• Was I wasting money somewhere?
• Were my investments performing properly?
• Was I carrying too much debt?
• Was I making dumb decisions that future me would eventually discover and curse present me for?

At the very least, I figured I should know exactly what I had.

So I started with the obvious question: What is my net worth? and did what any reasonable person would do. I built a spreadsheet.

And what a mighty spreadsheet it was!

At first, it was simple. I put in every account, asset, and debt. It was finally all in one place. I updated the values once a month. My method was pretty simple:

Number goes up = good.
Number goes down = bad.

Finance!

For a while, this was oddly satisfying. Every month I’d log into my accounts, update the balances, and watch the spreadsheet do its thing.

But then the monster started to grow.

• Some accounts were in Canadian dollars. Others were in US dollars. Fine. Add currency conversion.
• Were my investments actually performing well? Add investment tracking.
• But wait. How much of the return was actual investment performance and how much was currency movement? Another formula.
• What about taxes? Fees?
• Debt-to-asset ratios?
• How much liquidity did I actually have?
• How exposed was I to a market downturn?

More questions, more formulas.

I’ve been writing software for more than 30 years, so somewhere along the way the spreadsheet became another programming language. I’m not saying that was smart. It just happened the way these things always happen.

One innocent little formula at a time.

Then the questions changed

Knowing what I had wasn’t enough anymore. Now I wanted to know what I should do.

Should I pay off a mortgage or invest the money instead? Should I borrow against assets while rates were low? What happens if rates rise or markets drop 30% after I make the decision?

Then the questions got more personal.

Could I buy that car without doing something stupid to my future? Winters are cold. What if I wanted to disappear somewhere warm for four months? I’d never done that before.

Life is short. Could I do that without setting myself back?

Every decision created another question.

Every question created another model.

Pretty soon I wasn’t updating the spreadsheet once a month anymore. It became weekly, then almost daily. Like any other obsession, it crept in slowly.

I changed assumptions. Tested decisions. Checked what happened if markets fell. Checked what happened if interest rates rose. Checked whether one decision left me stronger or weaker than another.

At some point I stopped and thought:

Why am I doing this every day?

What am I actually looking for?

The question behind the questions

It wasn’t really about charts. After all, nobody wakes up in the morning thinking, Wow, I really want to see more charts today.

Well, no sane person.

I wasn’t building increasingly elaborate spreadsheets because I had developed some deep emotional attachment to debt ratios.

Well, maybe partly.

I was really trying to get rid of uncertainty.

Somewhere underneath all those calculations was the core question I hadn’t recognized yet:

Will I be okay?

Will I be okay if markets fall?

Will I be okay if rates rise?

Am I missing something?

Is there some risk hiding across all these accounts that I don’t see?

Am I making good decisions, or just “good in this moment” decisions?

Can I spend the money?

Can I take the time off?

Can I take more risk?

Should I be taking less?

That was what I was really trying to answer.

And the strange part was that I had every advantage. I had financial experience, software experience, spreadsheets, advisors, tax lawyers (so many lawyers!), and access to sophisticated tools.

I still found myself asking the same basic question everyone asks:

What should I do?

That was when I realized my spreadsheet had become a poor, brittle solution to a bigger problem.

I knew I wasn’t alone. Someone must have built a better way.

Surely this problem had already been solved

So I went looking.

There were plenty of financial apps. In fact, too many! Budgeting apps. Net worth trackers. Investment trackers. Cash-flow tools. Reporting tools.

I tried the obvious ones.

Some were excellent at budgeting. Others made it easy to connect all your accounts and see everything in one place. Most had beautiful charts.

Lots of charts.

OMG, charts everywhere!

I suppose all of that was useful. But I kept running into the same problem.

The charts would show me my cash flow. Great. Is my cash flow good?

They would show me my debt. Neat. Is that too much debt? Is it expensive debt? Should I pay it down or could that money be working harder somewhere else?

They would show me my investments. Fantastic. Are they actually performing well? How much risk am I taking? Am I accidentally concentrated in something across different accounts and funds?

They would show me my net worth. Awesome. But am I on the right path?

These apps had managed to replace my spreadsheet with pretty dashboards. I suppose that’s progress. At least I wasn’t manually editing things anymore but I still had to interpret everything myself.

The data was there. Oh, so much data!

The answers weren’t.

So I tried AI

This got much closer.

I connected my accounts and I could ask real questions. Should I pay down debt or invest? What happens if rates rise? How vulnerable am I to a market downturn? How much could I spend without putting something else at risk?

A good AI could give me genuinely useful answers.

For the first time, the computer wasn’t just displaying information. It was reasoning about it. It even made a few jokes. That was fun, and it felt important but once the novelty wore off, another problem became obvious.

AI only answered the questions I asked.

What about the questions I didn’t know to ask?

If I had hidden concentration risk buried across several investment accounts, how would I know to ask about it?

If I was carrying debt that looked harmless but was costing me far more than I realized, what would prompt me to ask?

If my spending had been creeping up faster than my income, but I hadn’t noticed the pattern yet, who was going to tell me?

If there was an opportunity that could materially improve my finances, how could I ask about something I didn’t know existed?

That was the aha moment.

The problem wasn’t access to more financial data. We already have lots of that. It wasn’t even access to answers anymore. AI was solving that.

The bigger problem was:

How do you know what matters?

Tracking was only the beginning

Most financial software is built around a model that made perfect sense twenty years ago:

• Connect your accounts.
• Bring everything into one place.
• Categorize your transactions.
• Create a budget.
• Show some charts.
• Run some reports.

That was a huge improvement over logging into ten different bank websites or maintaining everything by hand.

Today, I think that’s just the starting point. It’s certainly not the destination.

Of course a financial app should know what you own. “Everything all in one place” has become the default promise of almost every financial app out there. And that’s useful but it’s table stakes now.

Of course a financial app should understand your transactions, debt, investments, spending, cash flow, and net worth. The interesting question starts after that:

Now what?

What should I pay attention to? What am I doing well? What could I improve? What am I missing? Where am I exposed? Where is money being wasted?

What happens if the economy changes?

What happens if my life changes?

And when I’m making a major decision, how does that decision change my future?

That became the philosophy behind Knoware.

What I wanted Knoware to do

I didn’t want to build another financial dashboard.

Knoware should absolutely connect your accounts, track transactions, create budgets, follow investments, and calculate your net worth.

But those are inputs.

The point is what happens next.

Knoware should look across your finances and tell you what you need to know without you asking.

It should find opportunities you may be missing.

It should warn you about risks you haven’t noticed.

It should help you understand whether your finances are getting stronger or weaker.

And when you’re facing a decision, it should let you test that decision before you have to live with it.

What happens if I buy the house? Pay down the mortgage? Invest the cash? Take the year off? Borrow the money? Retire earlier?

What happens if everything goes according to plan?

And what happens if it doesn’t?

That is much closer to what I had been trying to build in that increasingly absurd spreadsheet.

Not better tracking. Not more data.

Better understanding and, ultimately, better decisions.

The part that matters most

We don’t track money because tracking money is fun. At least I don’t.

We do it because money gives us options.

Security. Freedom. The ability to take a risk. The ability to say no. The ability to say yes when something really matters.

The ability to stop working for a while. To help someone we care about. Start something new. Buy something ridiculous.

Sleep better at night.

The numbers matter because of what they let us do and I think our financial tools should reflect that.

They shouldn’t just tell us where our money went. They should help us understand where we’re going.

That’s why I built Knoware.

Not just to show you your money.

To help you know what to do with it.