Effective Milestone Driven Programming for Entrepreneurs, Jesse Rodgers


Programming that promises to help founders find success is pretty much everywhere. Organizations that deliver programming sprout up at a local level almost daily and they are too numerous to list. Generally speaking, all these programs offer some education and a few offer an accountability process to move businesses forward. The best programs have a high cadence where a founder achieves key growth metrics that de-risk the business and get things moving in the right direction. The worst programs hand founders a generic manual and leave them to figure it out.

A long post on effective milestone development and success factors for startup support / accelerator programs. Jessie has run them at CDL and at Volta on the East Coast and has a long history of Canadian startup community building.

I really liked the introduction of “judgement” as a factor. That is, are there people who have actually built, invested in, and supported successful startups who can supply that judgement in running a program to support early stage companies.

He also wraps up with some thoughts on COVID at the end, and what that means for “local” programs:

With COVID pushing everything online, the quality of programming at a local level is very much front and centre. What that means is tough to guess.

This is, in part, a response to Alex Danco’s post which specifically called out milestone based thinking — but covers a lot more ground on the past and future of these types of programs.

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pulling my seat up for this one as it’s topical for my roadmap. I agree that proximity, at least from a network perspective, doesn’t always need to be physical but there’s something to be said in placing judgement on action based on physical in-person observation. I think it’s easier to put your best face forward virtually and harder to hide behind the curtain in person.

I also like judgement over timelines. will read more into this…

So you watch your team type code over their shoulders? :stuck_out_tongue:

I’m a big fan of in person. But the fact is, like e-commerce, remote first and asynchronous targets a much larger pool.

But there’s a bunch of different directions this can go. Can you build a world class program anywhere? Yes. Think about what the most impactful usage of synchronous in person time is.

We’re probably going to have to get into specifics from here.

that’s SaaS world talkin’ :wink: software can be written at the beach. I’m specifically talking about the ecom vertical, and there are certain parts of that cog which have real physical limitations. Logistics, fulfillment, warehousing, shooting creative (photo, video, etc), community (to a certain degree).

I actual ended up thinking about this some more and the twitter post I tagged you on I think sums it up:

We can mix and match remote & local now that the remote work barrier has been breached

So: yes to in person and new kinds of “coworking”, “co-venture building”, and specialized shared services.

And yes to: mix and matching the best startup support programming AND judgement from all over.

Heck, great video conference rooms – not just shitty Zoom laptops – are probably way better for certain kinds of presentations to be given or received.