Whose success are you actually chasing?

I ask the questions no one else will.

I'm Nathan Biles, an entrepreneur and CTO with 25 years of building companies. Investors, advisors, the market and the people closest to you all have answers for you. I ask where those answers came from, so the success you chase is built on what you actually believe.

Start a conversation How I work

A session, in five lines

Illustrative example

F

We're raising this year so we can hit ten million in revenue by 2028.

Who decided ten million was the number?

F

Our investors, mostly. It's what the market expects.

If no one were watching, what would you actually want to build?

The redirect

F

Honestly? Something smaller. Something I'd still want to run in ten years.

The plan didn't change because of an answer. It changed because of a better question.

I don't hand you answers. I ask better questions.

No two conversations look the same, because no two decisions are the same. The work is an investigation: we follow the questions wherever they lead.

Bring it

What you keep circling

A decision, a direction, a doubt you haven't said out loud yet.

Investigate it

Question by question

We pull the assumptions into the open, and I don't let the easy answer stand.

See it

Clearly, on your terms

You leave knowing what you actually believe, and whether your plan matches it.

Questions we'll probably end up asking

Where did this goal come from: you, or everyone around you?
What would have to be true for this to be the right bet?
If AI did this part for free tomorrow, what would still be yours?
Which belief are you protecting by not deciding?
Who on your team disagrees, and what do they see that you don't?

An entrepreneur first.

I've spent 25 years building software and companies, as a founder, an architect and a CTO. Along the way I noticed the problems that mattered most were rarely technical. They were smart leaders heading in directions that didn't match what they believed, and not seeing it until much later.

I also stepped away from tech for two years to help a small city in Michigan become a better community of neighbors, working alongside city officials, schools, faith communities, nonprofits and local businesses. It taught me that the best work happens face to face.

Today I lead development with teams of AI coding agents, so I see firsthand what AI changes and what it doesn't. I'm based in Newport Beach and prefer to meet in person, over coffee or across a table.

Selected roles
CTO, TZ UnitedThe U.S. partner for institutions building on the Tezos blockchain.
Technology lead, CIMAAn AI-first marketing platform for mortgage lenders, built on ClickEngine, the attribution platform I created in 2019.
CTO, TendA neobank serving the U.S. and Mexico, with deposit accounts in both countries and cross-border money movement.
Architect, security startup backed by Michael DellDrove its merger into Secureworks, where the product became Taegis.
Open Threat Exchange, AlienVaultBuilt OTX from zero to over 100,000 users. AlienVault was acquired by AT&T.
Builder and consultant, 2001 to 2015Application development and consulting across industries, including data-driven products that learned from their users long before anyone called it AI.

In their words

Bring the decision you're stuck on.

I read every message myself and reply by email. You'll leave with clearer thinking, whether or not we work together.

Also from Alexandria Solutions

Daimon Classics

Classical philosophy, from Plato to Seneca, adapted into clear modern English with reflection prompts. Series One, edited by Nathan Biles. Read the books free at daimonclassics.com.