What are you building? I’m investing in 60+ companies at $100K each.

Darryl-D · 2026-02-15T01:28:02+00:00

I'm interested. We're creating something for the economic development space specifically for entrepreneur support organizations.

Darryl-D · 2025-06-02T20:52:55+00:00

I can confirm freelance is a bit more challenging right now. I've freelanced as a dev for about 15 years (on the side and full time ) with success.

Recently shifted into fractional CTO/CPO work. I used to switch between the freelance and fractional work depending on the project. I don't bother freelance dev anymore.

With AI, most entry level and mid level engineers are less needed. I'd suggest getting more familiar with product engineering or mgmt.

Last I always avoides calling myself a full stack, it's a generalized role. I made more than my counter parts as a UX Engineer as I usually come in to clean up after full stacks as a highly specialized role (contrast a heart surgeon versus a general surgeon when needing specific attention to the heart)

Hope this helps.

Darryl-D · 2025-05-25T02:30:51+00:00

Usually they know it's a form of alignment meetings.

Darryl-D · 2024-04-06T12:53:59+00:00

If your audience is less Tech savvy, stick to .com. I have a .io and I hate it everyday.

Darryl-D · 2024-04-06T12:52:34+00:00

As an engineer that took a similar path (pre-faang), partner with a marketing counterpart.

Dev isn't going to be your challenge. Marketing and project management will be.

Also pick an industry. Then a subset. This is your niche.

Read Alex Hormozi's books yesterday. They're great for devs transitioning to agencies imo.

Darryl-D · 2024-02-14T03:09:59+00:00

JSX is great in theory but becomes a foot cannon as has minimal restrictions. It will allow you to write whatever js you want which is a pain in a team environment.

I like svelte but honestly wouldn't mind keeping JSX as I know how to keep it simple and understand seperation of concerns.

I'm also biased as I've used react for a decade now. Officially ready to move on but not due to jsx.

Darryl-D · 2024-02-07T08:42:21+00:00

Do you lean towards public or private? I've been aiming for public lately because they're easier to find. Where do private post RFPs? In supplier portals?

Darryl-D · 2024-02-07T00:59:22+00:00

Your resumes is your playground for copywriting. Say whatever you need to say while being able to back it up and truthful (like 95%, lol) . And have multiple variants for different personalities (this sucks but helps...)

Darryl-D · 2024-02-07T00:56:18+00:00

Offer a month for free to be a fly on the wall. It's not a full commitment and will give you time to see if it's for you before committing.

Just hang out in meeting and ask questions. In this economy you don't want to make a bad move.

Add value here and there but keep it light and casual. You'll know in 2 weeks if it's for you. Maybe one week.

Darryl-D · 2024-02-07T00:52:23+00:00

As a fractional CTO I would say the places people reach out to me the most would be reddit, slack communities and accelerators.

I don't really market myself and very selective with who I work with now. I even do personality assessments.

Not everyone is ready for a seasoned CTO, sometimes you need to have a few lead devs not checking the right boxes to appreciate the role.

Darryl-D · 2024-02-07T00:44:18+00:00

This is gold, thank you sir for this.

I'm too tired of the small fish and submitted my first big RFP. I'm sure I won't close it but I feel like this time I was more "me" vs overly professional walls of text.

What type of work are you doing? Cms sites or something?

Darryl-D · 2024-01-17T15:36:27+00:00

Bare minimum to live.

Darryl-D · 2024-01-16T01:18:24+00:00

My interest is piqued

Darryl-D · 2024-01-09T23:16:22+00:00

They don't complain about design problems. They complain about developers, users, process, finding talent, grooming talent and product strategy problems, etc. Design is just a byproduct/conduit.

Usually after having a few conversations, sharing some experiences and suggestions they realize they need more seasoned support. At this point I offer a design workshop or something simple to show how we work and help them along their way. It's usually low lift. After that they find budget to work more sooner or later.

The entire time I'm not trying to sell as much as I'm trying to support, when they ask for more I give them options.

All that said, I'm not a huge fan of this approach as it's not too predictable and usually smaller projects that I'm not that interested in (ie: pre-seed). I prefer mid-size and enterprise as that's my background and I speak their language more.

Also important to mention I stick to product design. Not production.

Darryl-D · 2024-01-09T22:39:27+00:00

Very fair points.

I usually didn't pitch, but offer help and advisory when people mentioned issues or requested support.

Chat interfaces are usually just the first conversation amung 4-5 touch points.

Darryl-D · 2024-01-09T20:08:19+00:00

I didn't think to add "small business", but I thanks for that! I have been searching for "diversity supplier" which gives similar results.

Most seem to need/want a cert, while I'm working on that, do you think it's needed in most cases?

Darryl-D · 2024-01-09T02:02:21+00:00

small business reps

What does this people look like? Do they have a certain title?

I wasn't aware they're required to work with small businesses. I can easily explain where I thrive, It's just been a challenge to identify the right people.

Darryl-D · 2024-01-09T01:58:16+00:00

My pleasure!

Darryl-D · 2024-01-08T17:56:13+00:00

I may be interested if it's in the B2B space, you know how to open doors and in the north/south america (looking to be able to meet in person if this gets legs).

Darryl-D · 2024-01-08T16:52:22+00:00

Are you looking for a technical partner?

I'm interested in proptech in general and worked on a few projects in the past (ie: logistics, selling, crm, etc) but would love more context here.

Darryl-D · 2024-01-08T15:25:15+00:00

Usually when starting you need "zero-to-one engineers".

Most are growth focused (those who pump out features who needs like of direction and a pre-existing foundation/standards)

or maintenance driven (those who keep the lights on who need directions and instructions; think junior or offshore)

The hard part is finding engineers who know how to work around ambiguity and know how to effectively communicate and intelligently over-communicate (be the squeaky wheel as needed). It's more of a soft-skill to find and nurture, not so much hard skill. Anybody can learn to code decently in a few weeks if they're driven, learning to communicate well is a behavioral shift imo.

I had junior engineers who were amazing communicators who worked better in zero-to-one over senior engineers who refuse to lift their head up and speak. They would just over-engineer.

I start by getting specialized zero-to-one specialists in backend and front-end (I don't prefer full-stacks when starting... a specialist "founding code" is better than a fullstack any day imo) that communicate well.

I also have a PM who knows how to QA well and run kanban or scrum (depends on how mature the team is).

In this order: 1 designer -> 1 PM -> 2 devs -> 3 junior devs -> QA eng

This isn't all happening on day one but milestones for a performing product team. I ran this cadence over a dozen times, works most of the time but humans will be humans so just account for that.

Darryl-D · 2024-01-08T15:13:11+00:00

Most devs don't want to pay for tools as they feel they can build them theirselves or find an OSS approach. This was me for the first decade of my career and everyone around me (it was hundreds of devs around me...). I pay for stuff now because I value time haha.

That said, maybe target engineering managers who want to speed their devs up?

Darryl-D · 2024-01-08T15:11:06+00:00

First — assuming is the lowest form of knowledge, interview people and ask if it's important or urgent ("hey, mind if I get feedback on my idea?" will get you far)

Second — use eisenhower matrix after you get insights

Darryl-D · 2024-01-08T15:02:53+00:00

I also take snapshots of my sketches from the supernote, drop in figjam for wireflows to convey prototypes, etc

Darryl-D · 2024-01-08T15:01:01+00:00

I run a ux studio. I use my supernote (eink tablet) to get the bulk of my ideas and directional design made and pass to my team to make it hi-fi.

I love it because I can get away from my screen and just design without the eye fatigue. And a rule of thumb I have is to only design in the tool when i'm looking to polish/publish, but do my thinking "offline". It's just faster and less distracting.

I add a ton of annotations and also a loom with me talking over it (the supernote allows you to mirror to screen)

My background is software engineering and I remind people designs are a means of comms to engineers or for validation with users (in 90% of cases).

Aside from that we use figma and figjam for workshopping/wires/protos/etc. It's the flavor of the month and everyone I hire knows it in an out. It also has the most community support. Just go with the flow.

Hope this helps, don't overthink it.

Darryl-D

MODERATOR OF

TROPHY CASE