Multi-Project Entrepreneurship

Becoming a "Serial Entrepreneur"

I want to serve (firefighting). I want to be fit (hybrid athlete). I want to have the financial and time flexibility to spend meaningful time with my family. And I want to have a meangingful income.

• By metrics (not concrete, just something to talk against), I'd like to make >$300k in a year while working ~3 hour days.

• Based on my research of others who have done this, and the average failure rate of a business, it could take upwards of 12 project starts before they become successful

Right now, I can't achieve the above without overcommitting

• I am present with my family, though we have to spend more time on chores / housekeeping than I'd like because we can't pay someone to do that for us

• I have a part-time job that pays the bills, but doesn't meet my above income hurdle and doesn't have significant upside without significant time increases

• I have 2 hours / day I can commit to "side projects" that may produce income

• Between the part-time job, family, chores, and side hustle time, working out is difficult to put in

• Firefighting is impossible to fit into life with all of the above

What should I do about it?

I am taking inspiration from those who have done "12 projects in 12 months." I want to establish a means by which I can generate & test an idea to see if it has income-producing potential. Strategically, I would pursue this through an "audience first" lens, which means that I would find my potential customers before I would come up with an idea, and then generate an idea based on those customers' pains / needs / desires based on interviews / surveys I would do with them.

Tactically, I would start by targeting small opportunities that did not need much time / resources to stand up. After this, I would use the proceeds from an earlier project to leverage inputs into the later project.

Project 1: $500 in Monthly Revenue

• Gives me more time by being able to pay someone for basic chores

Project 2: $1,000 in Monthly Revenue

• May enable me more time further by paying for a digital assistant to help with some of the lower-value activities.

Project 3: $2,000 in Monthly Revenue

• Starts allowing me to hire consistent freelance work to help in future projects. This fast-tracks speed to market, while allowing me to remain in my day job to pay the bills.

Project 4: $4,000 in Monthly Revenue

• This is the stage at which I could start taking larger and / or more frequent bets into various projects while still involving freelancers.

Project 5: $8,000 in Monthly Revenue

• This, combined with the above, would enable me to stop my part-time job and continue to pursue this line of work.

• The standard here is to hold these revenue streams for 6 months OR have 3 years worth of expenses set aside before leaving the part-time work.

Project 6: $16,000 in Monthly Revenue

• By this stage, I will have hopefully achieved my income standard and will have enough experience in the "outsourcing" of the build-up phase that I can likely only work 3 hours / week.

• This stage also allows me the flexibility to test much larger projects: ones that may require investor involvement in order to succeed.

So What Does the Next Cycle (5 - 6 weeks) Look Like?

The main question looks to be: How many projects are reasonable to pursue at one time, knowing that I am going to be working on the Distillery during this time?

Tactically this looks like the list of to-dos below. Inspiration primarily taken from the here:

• Generating a list of 15 - 20 potential customer types that I have a natural interest in and may want to serve

• Pick the top 3

• Become "embedded" in those audiences via forums & other online mediums to determine their experiences / pains / needs / desires based on surveys / interviews that I would do with them

• Also create a landing page for those audiences to see how many sign up

• Create a Customer Journey Map to highlight the customer experiences in relation to some proposed desire / pain / need surfaced in customer interviews

• Create an Opportunity Map based on the assumptions surfaced in the Customer Journey Map, that creates a view of the features / products we would want to build

• Start testing assumptions with customers. Continue to test assumptions through testing with customers all the way up to building the actual product that generates income

Main Focus of Project

To generate the systems / processes necessary in order to succeed in a multi-project, entrepreneurial life, while knowing that any single project is more likely to fail than not. Deploying these processes within the context of little time / money initially.