Navigating the Software Startup Journey: Lessons from Raising Reimagined

So we have an idea… next step, figure out the execution plan. The plan was questionable at best and ever-evolving. It started with learning podcasts, books, articles, playing around with LucidChart, calling friends... How do I make a software platform? How do I drive software development? How do I deliver my idea in a way that even gets me good feedback? Do I need a domestic or global developer, blended rate? Piece a solution together or build from scratch? 

It started with research, full-stack development on LinkedIn learning and calls with our in-house experts (friends, family and anyone who would talk to us for free). First lesson learned, some people are just willing to help, don’t be afraid to ask for a phone call.

I (Paige), by nature am a slow and steady methodical planner, my husband (Ben) is a let’s make it happen captain as fast as humanly possible…

“Move fast and break things” -Mark Zuckerberg

A little concerning motto for your airline pilot, and scrappy startup up with little experience, backing and not to mention the fact that either of us are Mark freaking Zuckerberg but I digress.

As a Kentucky (not Silicon Valley startup *cough*cough BEN)… we decided we needed a combination of our two approaches.

We started to thrive under the motto of “Never ready, prepared enough.” -Paige

You will never know everything you need to know and we realized that by doing we learn the most, we can’t be careless but we can’t be bulletproof.

We started with calls with lawyers…

Remember that in-house talent, well my dad’s friend through works brother is a patent lawyer and he fielded our first call. Do we want to/can we file a patent (determined it would be a provisional patent - meaning it would only last for one year, requires few formal requirements and has a priority date of 1-year from the ideas disclosure).

In the end, we decided the time, effort and stage we were in in development made a patent at the beginning the wrong move for us (~$8k-13k). I made some basic UML diagrams from my research and understanding of how we wanted the idea to come to life on a platform, however, I realized it wasn’t detailed enough, I didn’t have the capitol to build it and defend a patent and I felt it would only slow down our time to market. We decided, someone may very well build it, but we had the tools to build it better.

I did, however, start calls making everyone sign an NDA (non-disclosure agreement)… I asked if we could use their ‘paper’ because all we had was a blanket agreement from the internet I slapped our names on since we still did not have an LLC and we were not paying for a lawyer.

So, we moved forward I slapped a confidentiality agreement message on all my messages and my slide decks and we let it fly; I didn’t want the red tape and our fear of a stolen idea interfering our pursuit of bringing our vision to life. We wanted this to start adding value to our family business and small and medium businesses alike as soon as possible. Besides, we have a year to build wireframes and get code that could help support a patent - let’s make something worth patenting in that time.

It developed into calls with software development teams and Upwork freelancers

We realized we couldn’t build it alone, we did try (I am not a Wordpress expert). So, we turned to a local development team to Louisville, Kentucky. They didn’t seem to believe in the idea or its potential and they seemed only happy in taking out money (quoting us $55k for a throw-away minimum viable product, MVP). It felt like a slap in the face, but we also realized maybe we weren’t pitching it well. We worked on better communication the idea and built some supporting material.

We were pretty disappointed, we wanted to work with that team but they didn’t want to work with us; it lit a fire under our ass for sure.

We went to Upwork and sought out a developer, we got LOTS of proposals and interest. We went on to seriously vet about 30 Upwork developers.

  • Built a Request for Proposal (RFP)

  • Built a slidedeck to get ideas across to developers

It ended with LinkedIn solicitation

After going through the Upwork proposals, we spoke to some great developers but mainly what we felt were designers or too small of teams to carry out the vision. We began questioning; do we build a throw-away MVP, piece something together on a Wordpress/Woocommerce, or do we start laying the code and architecture for a scalable product?

We went back and forth and we compared proposals for all the options.

It came down to three developers:

  1. A developer with a team in India

  2. A project manager with a leveraged team from both the US, Croatia and India

  3. A domestic, Milwaukee family-business

We went with 3, a company that got the vision and was excited to help us make it happen. They brought lots of thought to every call, they were very easy to communicate with, available and saw the potential that we saw. They were not the cheapest, but we believed in their ability to carry it out based on their previous work along with our communications. Our gut said go with these guys.

We could have vetted a thousand more developers, but I think we did our due diligence and were ready to get started.

Never ready, prepared enough

And an LLC was born - Raising Reimagined


We utilized Zen Business to establish an LLC in Delaware which had both of us as the ‘owners’ of the business [Raising Reimagined, LLC] and we moved forward with filing a for a trademark on “Raising Reimagined,” we did this ourselves through Legalzoom. We bought the domain and secured all domains around Raising Reimagined through Google Domains.

Raising Reimagined plans to sign an agreement to enter into a discovery phase with company 3; blastoff.

First logo for Raising Reimagined by another in-house talent, a longtime friend and talented creative Nikki Slivka.

First logo for Raising Reimagined by another in-house talent, a longtime friend and talented creative Nikki Slivka.

Paige Miller

Hello! I'm Paige, the co-founder of Raising Reimagined and the voice behind our blog. With a passion for innovative fundraising and a heart for community engagement, I merge tech-savvy solutions with heartfelt storytelling. My mission? To empower schools, fire companies, and local organizations with insights and strategies that turn fundraising goals into remarkable successes. When I'm not brainstorming the next big idea for our platform, you'll find me actively involved in community events, always seeking new inspirations to bring back to our readers.

https://sites.google.com/view/paigemillerxyz/home
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