Advisor · Investor · Mentor · Tech-Obsessed
Get the reality.
Most founders don't need more encouragement. They need someone who has been in the chair to tell them what is actually true about their company - while there is still time to do something about it.
“Reality is that which, when you stop believing in it, doesn't go away.” Philip K. DickGet Real Now
Why this exists
Candor is the scarce good.
An AI founder can find enthusiasm almost anywhere right now. Investors who are being polite. Consultants billing by the hour. A chatbot that thinks every idea is excellent. What is genuinely hard to find is someone who will look at your moat, your burn, your team and your odds, and then say the unwelcome thing out loud.
I have been on both sides of that conversation. I have raised money on a slide I could not fully defend. I have been the CEO who was certain the pivot was working. We are all capable of believing our own deck - that is not a character flaw, it is what it takes to start something. But it is expensive when nobody checks it.
So that is the job here. Not cheerleading, and not a sixty-page strategy document nobody opens twice. The honest read, delivered early enough to be useful.
The approach
How I actually work.
Four decades in technology taught me that most advice fails for the same reason: it arrives too late, too general, and too flattering. This is built to avoid all three.
We establish what is true before we discuss what to do
No strategy survives a wrong premise. We start with the facts of your business - what the product really does, where the revenue really comes from, what the metrics look like without the framing. Usually this takes one conversation. Occasionally it ends the conversation, which is also a result.
The bad news comes first, not last
If something is broken, you hear it at the beginning while it is still cheap to fix, not buried on slide forty after the encouraging part. I would rather be uncomfortable in week one than agreeable for six months.
Course corrections, not grand plans
My father was in Special Forces and the family motto was adapt, improvise, and overcome. That is closer to how companies actually get built than any five-year roadmap. We find the next real decision, make it well, and then find the one after that.
You keep the thinking, not just the answer
The goal is a founder who can run the analysis without me next time. I would rather hand you the framework and lose the retainer than build a dependency and call it a relationship.
What to expect
Outcomes I will stand behind.
These are the things a good engagement actually produces. They are deliberately not expressed as percentages, because the honest version of this work does not come with a guaranteed number attached.
- A defensible answer to “what is actually ours?” If your entire technical advantage can be rebuilt by a competent engineer over a weekend, your moat is something else - distribution, proprietary data, switching costs. We will find it, name it, or conclude honestly that it is not there yet.
- A story that survives diligence. Not a better-sounding narrative - a narrative that still holds when a partner starts pulling on the loose threads. We find those threads before they do.
- Fewer months spent on the wrong thing. The most expensive line item in an early-stage company is not payroll. It is the quarter you spent building something nobody was going to buy.
- A clear read on whether to raise now, later, or at all. Including the case where the honest answer is that you are not ready, which is a genuinely useful thing to learn from someone who is not being paid to place the round.
- One person who will tell you the truth. Permanently. Long after the engagement ends, you have someone to call before the decision instead of after it.
And what I will not promise
A valuation. A term sheet. A funding outcome. A percentage. Anyone promising you those is selling you something, and the fact that it is a comforting thing to be sold is exactly why it works.
Fit
Who this is for.
Early-stage AI founders
Pre-seed through Series A, building something AI-native. You have a product and some interest, and you are somewhere between eighteen months and six weeks away from a hard truth about whether this works. You would rather find out now.
Investors and funds
You are seeing far more AI deals than you can properly evaluate, and it is genuinely difficult to tell a defensible technical moat from a thin wrapper on somebody else's model. You want an operator's read before the wire, not after.
Who this is not for
Founders who want validation, a warm introduction, or a document to wave at their board. That work exists and other people do it well. If what you want is agreement, we will both be frustrated inside of a week.
How we would start
One conversation, no charge, no deck required. Bring the thing you are actually worried about - not the polished version. If I can be useful we will talk about what an engagement looks like. If I cannot, I will tell you that too, and point you at whoever can.
Who is telling you this
Preston Callicott
I am a self-described tech humanist who has spent roughly four decades in technology and thirty-five years inside startups - which mostly means I have made, or watched closely, most of the mistakes available to an early-stage company.
My career started at Hewlett Packard, Advanced Micro Devices, and Price Waterhouse's management consulting practice. In 1990 I found startups and never really recovered; since then I have been a founding-team member of more than a dozen of them. I spent a decade as CEO of Five Talent Software in Bend, Oregon, building custom software for companies whose whole future depended on getting it right.
Alongside that I spent years writing a monthly technology column for Cascade Business News and The Bend Bulletin - on artificial intelligence, quantum computing, chip supply chains, facial recognition, robotics. Writing a column every month for years is a useful discipline for an advisor: everything you predicted is still sitting there in print with a date on it.
One of those columns has aged well. In 2019 I wrote about running an entire company from a smartphone with “embedded e-bot team members such as an Executive Assistant, COO, CMO, CIO and CTO.” I coined the term e-bots and proposed taxing them at the wages of the humans they replaced. Seven years later that is roughly the product category the industry is racing to build.
Others have aged less well, and I will happily walk you through those too. That is more or less the point of the name.
I live in Bend, Oregon, which I chose deliberately over Marin County because I wanted my kids in a real town with real people. I have served on boards including Looking Forward, Opportunity Knocks, the Bend Chamber, EDCO's expert board, and OSU-Cascades, where I have also given the commencement address. My wife Chelsea and our twins remind me regularly that work is not everything.
Live thinking
My investment thesis, republished every week.
I keep a public board of what I believe about where value is accumulating in AI - the five layers I evaluate against, the market evidence behind it, and which way that evidence moved this week.
It updates weekly for an unglamorous reason. When I re-checked my own April research against primary sources, seven figures had to be dropped and eight restated - one was overstated by a factor of about 170, and a regulatory deadline the whole argument leaned on had been moved by sixteen months. A thesis nobody re-checks is just an opinion with footnotes.
So the board shows the weeks my thesis got weaker as prominently as the weeks it got stronger. That is the part most people leave out, and it is the only part that makes the rest worth reading.
Get real now
Bring me the thing you're actually worried about.
Not the pitch. The part you would skip if an investor asked. One conversation, no charge, and a straight answer at the end of it.