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Dakota now runs more than 30 events a year. Five years ago, that number was one.
The gap between those two numbers isn't budget or headcount. It's five roadblocks that stop most firms before they ever book a venue.
If your firm has talked about hosting an event for longer than it's taken to actually host one, you're probably stuck on one of these.
1. No Clear "Why"
Most event planning starts with logistics: venue, date, guest list. It should start with a simpler set of questions: who, what, when, where, and why. Who is the event for, what does the audience look like, what is the firm trying to accomplish, where does it make sense to hold it, and why host it at all.
The "why" gets skipped most often, and it's the one that matters most. A clearly documented why becomes the tiebreaker later. When the team disagrees on a decision mid-planning, whether that's guest list, format, or venue, the original objective resolves most of it. Skip that step, and every disagreement has to be litigated from scratch.
Answer the why first. Everything else should follow from it.
2. Too Many Stakeholders
A first event usually needs sign-off from marketing, sales, compliance, and often a regional head or two. Too many opinions in the planning process make it difficult to define and target the event in the first place, and multiple layers of internal approval compress an already short timeline. Planning an event two months out while collecting sign-off from several parties leaves little room to execute well.
Alignment has to come before planning starts, not during it. Everyone internally should be working toward the same goal rather than acting as a barrier to it.
3. ROI Paralysis
Firms frequently fixate on the return of a single event to the point that it prevents them from running one at all.
Dakota's own experience shows why that's the wrong instinct. Early on, Dakota tested events in Detroit and Birmingham, saw weaker turnout in both, and pivoted. That's a normal part of building a program, not a signal to stop.
The first event only has to answer one question: whether there's a second one. It doesn't need to prove the whole program works, and a large goal isn't a prerequisite for starting.
4. Starting Too Big
An ambitious multi-city, multi-event vision feels like the responsible way to pitch an events program: show leadership the full plan, get buy-in for the whole thing at once. In practice, a vision of 50 events a year will overwhelm the team before it's built anything, and it creates internal conflict that a single event never would.
Start with one, not five. A single well-run event proves the team can execute, and it's what earns the room to plan the next one.
5. No Process for Earning Trust
The firms that eventually run events without needing sign-off for every detail all did the same thing early on: they documented everything from day one. Dakota still refers back to the notes taken on its first five events in 2021.
That record is what converts a one-time approval into standing trust. It usually takes just one or two well-run events to bring internal stakeholders on board, and five years in, Dakota's team now makes many event decisions without internal review, because the groundwork already established what they can and cannot do.
Just Start
Every one of these roadblocks points to the same fix: stop planning for the program and start planning for the event. Answer the why, get alignment early, treat event one as a single data point, keep the first one small, and document it well enough to earn the next one.
Nothing about a first event will be perfect. As the Dakota-ism goes: throw your hat over the wall. Whether it becomes a 30-events-a-year program is a decision that can wait. It's not one you have to make before you host your first event.
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