The Book
True North
My thinking on what to do when the assumptions that got you here no longer match the world you’re operating in now.
Read True NorthStrategic perspective for established founders
Sometimes the hardest business problems are the ones you’re too close to see.
Octavian helps business owners figure out what’s really going on, what they may be overlooking, and where their time, money and attention should go next. Whether something isn’t working, you’re trying to grow, or you simply have more possibilities than clarity, I bring an outside perspective to the whole business and help you find the next move that actually makes sense.
“The opportunity you're looking for may already be sitting inside your business.”
ANDREA OLIVER · FOUNDER, OCTAVIANThe Octavian View
A lot can change while you’re busy running the business.
The market changes. Customers change. You change. And over the years, you accumulate skills, offers, relationships, ideas and ways of doing things that don’t always fit neatly into the plan you started with. I look at the business as it exists now, not as it was supposed to look by this point.
01
Start with what’s actually happening.
What’s working? What isn’t? Where is the business making things harder than they need to be? That matters more than staying loyal to an old plan.
02
Look at what you’ve already built.
Years in business leave things behind: expertise, customers, relationships, reputation, methods, old offers and ideas that may still have value.
03
Decide what deserves attention now.
You can have several good ideas and still make a bad decision about where to put the next six months. Part of the work is deciding what matters now and what can wait.
Why Octavian
I don’t assume I know the answer before I’ve looked at the business.
A lead problem, a revenue problem, a growth problem and a founder who feels stuck can all look obvious from the outside. They aren’t always what they seem. My job is to look closely enough to find out what’s actually driving the situation before deciding what should be done about it.
Sometimes growth is the wrong first move.
If something underneath the business is weak, adding more customers, offers or complexity can make the problem more expensive.
Sometimes you already have what you need.
Before I tell someone to build something new, I want to know what they’ve already earned, learned, created and left sitting on the shelf.
The obvious problem may not be the real one.
When something keeps resisting the fix, I go looking for what’s happening underneath it.
The founder matters too.
A business can make money and still be built in a way that leaves the owner carrying far too much of it personally.
Meet Andrea Oliver
I built Octavian because I learned what a business looks like when the owner suddenly can't carry it.
Before Octavian, I had built a seven-figure business. Then a 2019 car accident took me out of it for an extended period and changed the questions I asked about business permanently.
After that, I stopped being impressed by growth on its own. I became much more interested in whether a business could hold up when life changed, how much of it depended on the founder, and whether all that work was actually leaving the owner in a stronger position.
Founders know the history of their businesses better than I ever will. I get the advantage of coming in without years of assumptions attached to it. I research, ask questions, follow the threads that look important, and often notice connections that are difficult to see when you’re standing in the middle of them.
You know the history. I get to see the pattern.
The Work
Business owners usually come to me when they know something needs to change, but they aren’t sure what deserves attention first.
Sometimes something is clearly wrong. Other times the business is fine, but the owner can see several possible directions and doesn’t want to spend the next year betting on the wrong one.
Something keeps not workingWe figure out whether the problem you can see is actually the problem you need to solve.
You know there’s more here, but you can’t quite see itWe look across what you’ve built and see whether there are useful connections, overlooked assets or opportunities hiding in plain sight.
You have too many reasonable optionsWe look at the tradeoffs and decide which move deserves your time now, and which ones don’t.
You’ve outgrown the business you originally builtWe work out how to move toward the bigger vision without trying to tear everything down and rebuild it at once.
See How I Think
Don't take my word for it. Spend some time with the work.
You don’t have to hire me to find out whether the way I think is useful to you. The book and podcast will give you a pretty good idea.
The Podcast
Watch the thinking in motion.
I pull apart businesses, founder decisions and changes in the market to see what they can teach us about making better moves.
Listen to the PodcastSpend a little time with either one. You’ll know pretty quickly whether you like the way I look at business.
When You're Ready
Not every business needs the same kind of help.
If you already know what’s bothering you, start with the offers and find the closest match. If you’re not quite sure what the problem is yet, that’s okay too. Sometimes figuring that out is the first piece of the work.
AUGUSTUS
“I found Rome a city of bricks and left it a city of marble.”
Augustus Caesar