All day, everyday, I speak to early stage founders, thats it. After over 1,000+ intro calls with founders seeking a startup consultant, I’ve seen every mistake in the book. Whether we end up working together isn’t the point. Here’s MY truth and what I tell anyone I speak to about choosing the right consultant for your startup journey.
For me, I require a few dates. A few working sessions. A chance to play and explore and make sure we’re a great match and i can absolutely not only drive accretive value but that we will enjoy the process. You cannot hire me on the first date. Period. WE have to WANT to work with each other equally – I need to be as excited to learn, explore, understand and work with you as you are with me.
If we do this right, I will learn as much from you as you from me – if I’m lucky, I might even learn more from you. It’s a peer relationship, it is NOT a student-teacher relationship. Read that again.
I assume competency, but that comes from having been in the trenches and having the stories to prove it. I know how good I am, I have the stack of receipts doing it for myself and working with founders, but that’s not the point.
Some things I think you should run from:
The “Success Story” Consultant sits across from you, rambling about how they scaled their last startup to millions. They’re selling you their story, not listening to yours. These are cracked mirrors – their reflection might look pretty, but it’s distorted. Your journey isn’t theirs, and anyone trying to copy-paste their success story onto your business is selling you snake oil.
There is no proven playbook. There are guides and best practices but every founder, with every startup is playing a different game, different rules, different market.
The “Process Police” will show up with their fancy frameworks and rigid systems. They’ll try to force your messy, dynamic startup into their neat little boxes. But innovation doesn’t happen in boxes. Growth doesn’t follow a predictable pattern. You need someone who can think on their feet, not just follow a checklist.
You need a startup consultant who:
Listens more than they talk. I mean really listens. When you’re explaining your market challenges, they’re not just waiting for their turn to speak – they’re connecting dots you didn’t even know existed. They ask questions that make you stop and think, “Damn, I never looked at it that way.”
Goes down rabbit holes with you. You start with pricing because you think thats the most important topic and end up completely reimagining your onboarding experience. That’s the kind of exploration that creates breakthrough moments.
Gives you room to breathe and think. Sometimes the best consulting happens in silence, when we’re both staring at a whiteboard, letting ideas marinate. If someone’s filling every second with talk, they’re probably selling rather than solving.
Half the value of these sessions is just talking out loud. Let it all be wrong. Who cares. Seriously. The magic isn’t in being right – it’s in the willingness to put ideas on the table when you’ve got seven million other priorities screaming for attention.
The freedom to not be apologetic about “thinking out loud.” That’s exactly what we should be doing. Maybe we’re hearing these ideas for the first time. That’s the point. It’s about achieving unbelievable alignment with zero assumptions. Sometimes the most valuable thing I do is create space for conversations that should have happened months ago but never did because everyone was too busy “executing.”
This is the secret sauce: We can have those wild, open brainstorming sessions – those beautiful chaos moments where anything seems possible – precisely because we’re grounded in reality before and after. We never let excitement beat opportunity. Being able to dream big only works when you’re strong enough, clever enough, clear enough, and unified enough to be absolutely ruthless in prioritizing what matters.
Even when the “best new idea ever” pops up (and it will), we have the discipline to put it through the same rigorous filter as everything else. I’ll get just as excited about your ideas as you do, but I’ll also be the first to help you kill them if they don’t serve your core mission.
This isn’t just about qualifications – it’s about chemistry. Here’s what to watch for:
Information Reception: Does their style match your learning pattern? Some need everything in visuals – flow charts, diagrams, sketches. Others prefer rapid-fire verbal spitballing. Others like time to think and reflect. Neither is wrong, but they needed different types of communication styles.
Communication Patterns: Watch how they handle disagreement. Do they bulldoze through with their opinion, or can they hold space for productive conflict? This is not wrong or right, it’s spending time unpacking why, exploring alternatives, and building something better together – sometimes awful ideas are the groundwork for epic ideas.
Interruption Style: This one’s subtle but crucial. When they cut in (and I like), is it to redirect you when you’re going off track, or to force their point? Good interruptions feel like course corrections, not conversational hijacking.
Thinking Process: Some consultants are linear thinkers – A leads to B leads to C. Others are connectors, pulling insights from seemingly unrelated areas. Watch how their mind works. Does it complement your thinking style or clash with it?
Obsession Points: Pay attention to what gets them excited. If they light up only when talking about their methodology but glaze over when discussing your specific challenges, that’s a problem.
Here’s how to measure what matters:
References That Count: Don’t just ask for references – ask for references from founders who were in your shoes. If you’re a pre-seed B2B founder, talking to a Series C D2C founder about their experience won’t tell you much. I connect potential clients with founders who were exactly where they are now.
Progress Metrics: Track specific improvements. Are decisions getting made faster? Are you closing deals quicker? Is your team executing more effectively? There has to be measurable output.
Do a working session. No bullshit about “we can’t, it’s not long enough, I don’t know you enough” – fuck that. Jump in. Get dirty. Get messy. Real generalists don’t care and are agnostic. You just want to see if a few good ideas come from it.
Done right, it might not be a lifelong financial relationship, but it should and would be a lifelong personal relationship. So we both have an obligation to take the time. Time is relative.
Every call should leave you energized, not drained. After a recent session, a founder told me, “For the first time in months, I feel like I know exactly what to do next.” That’s the feeling you’re after. If you’re not getting it, don’t waste another minute – hang up and keep looking.
Remember: Finding the right startup consultant is like finding a co-founder for a specific chapter of your journey. Take the time to get it right. Your company’s future might depend on it.
Why do you charge for the intro call?
On our first call we jump straight in. Let’s work on a problem, architect the start of a strategy or just explore exploring.