My Startup Challenge 2023 Roadmap

Time to focus on nurturing these seedlings.

Many aspiring entrepreneurs, from developers to service professionals, are starting many side projects but never completing them. Myself included.

Recently, I came across the startup 12-month challenge popularized by Pieter Levels. And also decided to give it a try. However, I want to build on this and refine it for my specific needs.

So what is this challenge?

The original idea is to launch a new startup monthly for the next 12 months. The goal is to get used to building things quickly and promptly instead of getting fixated on creating the perfect product that never ends up seeing the light of day.

DIY challenge modifications

The focus is building around what I already have toward short-term product development for quick revenue generation. The goal is to dust off the proverbial dust from the brands I’ve been baking on and off over the past few years to #BuildBackBetter by the end of 2023.

Change 01: Rebuilding the core business components (e.g., business model, product portfolio) for each brand. If I want each brand to have its POC to help run operations, then they need to become self-sustaining and have a focus on sustained YoY growth outcomes specific to the brand.

• Massive Transformative Purpose
• Business Model
• MVP

Change 02: Launching intentional experiments and building out a dedicated team. Since my zone of genius is in #RevOps (GTM Strategy and Operations), I’ll be developing an async workflow and leveraging staff on demand for capacity building to #DoMoreFaster.

• Team Structure
• LEAN Sprint

Change 03: Focusing each quarter on a [H] brand development sprint with related OKRs. I work off contractual projects now and have a baby debuting in February 2023. To make this roadmap achievable, I’ll cascade the brand items across the quarters to narrow the focus with some relevant Objectives & Key Results (OKRs).

• OKRs
• Execute, Execute, Execute

Sprint 1 focus

Next, I’ll define the first sprint timeline as a quarter (3-months) to timebox my efforts.

Stage 1: Problem/Solution Fit (PSFit)

• Understand Problem (Insights)
• Define Solution
• Craft Offer
• Build MVP

And I’ll bake in the tried and true Techstars method of executing numerous experiments for greater outcomes.

LEAN Sprint method

• Expose Problems
• Define Solutions
• Short-list Solutions
• Test Solutions
• Decide on Solutions

Note: while I have timeboxed the first stage/sprint, it is a means to an end and not the end itself. I am also baking in the Founders Institute focus on achieving $1MM ARR within 18 months. In this way, Sprint 1 (PSFit) will tee up Sprint 2: Product/Market Fit (PMFit).

Defining Progress

While learning is a key activity, it’s the results that matter.

— Ash Maurya

There’s a lot of waste in the startup journey. To be the right kind of busy, we’ll follow Ash Maurya’s six-step meta-framework (Scaling Lean), or the ‘GO LEAN’ mnemonic, to effectively define, measure, and communicate progress.

Goal
Observe and Orient
Learn, Leverage, or Lift
Experiment
Analyze
Next Actions

👁‍🗨 Traction is the rate at which a business model captures monetizeable value from its users.

Traction will be the main protagonist of our business model narrative. I lean towards concentrating on repeatable actions users take (leading indicators) to extrapolate future business model growth.

👁‍🗨 Customer throughput is the rate at which nonpaying users are processed into paying customers.

I’m also leaning towards measuring customer throughput (people) as more tangible and actionable than measuring throughput (fuzzy revenue number) at this early stage. This single measurement goal will help me focus on my mission to build products that matter (successful products).

Sprint 1 Objective: Build a working business model

• Key Result1: Define traction
• Key Result2: Map out five customer factory steps
• Key Result3: Run 4 LEAN Sprints
• Key Result4: Produce a validated traction model

I’ll update the list below with the different startups as I go along.

[H] The Hibernating brands

These are my brands that have been incubating over time.

#H1 STVNRCO — My personal brand

I have a personal brand, something I’ve been maintaining diligently so that I never lose my identity when parting ways with a job or title. There’s some potential, so let’s see how we can shape it.

• Status: Launched
• URL: https://stvnr.co
• Read the [project debrief] here (coming 12/16)
• Brand affiliations: 1 Million Cups Organizer, CMX Hub B2C Professional of the Year, CUNY Startups Mentor, FoundersBoost Chapter Director, Founders Institute Mentor, Global Entrepreneurship Week US Delegate, InterNations Organizer, HireRunner Operator, iNNPulsa Colombia Mentor & CEmprende Ambassador, Kauffman FastTrac Facilitator, OpenExO Ambassador/Sprint Coach, Right To Start Ambassador, Rutanio Ambassador, Solana Collective Ambassador, Startup Huddle Facilitator, Techstars Mentor, Techstars Startup Weekend Facilitator, WeWork Labs Mentor.

#H2 SUEGO — An amalgamation of everything I’ve been doing across community building since 2015

I needed a vehicle to house startup programming and event funding over the years. And I’ve shaped it more thanks to a fantastic cast of rockstar [advisory board] members over the past year. But now it’s time to be serial about making this a more singular pursuit and focal point in 2023.

• Status: Incorporated LLC
• URL: https://suego.co
• Read the [project debrief] here (coming 12/16)
• Brand affiliations: 1 Million Cups, BOGOWEEK, CMX Connect, ExO Meetup, Freelancer’s Union SPARK, FoundersBoost, Global Entrepreneurship Week, InterNations Bogotá Entrepreneurs Group, Kauffman FastTrac, National Entrepreneurship Week, Startup Huddle, Techstars Startup Weekend.

#H3 BloomShift — A dba under SUEGO that has strong connections to HubSpot and the community challenge around Digital Marketing

The initial market problem identified turned into a digital agency experiment that sustained me during an Eastern Europe remote work sprint in 2019. Then it took a backseat as I went on to support Techstars and 1863 Ventures as an employee. I’ve kept it intact with the official HubSpot Solutions Provider certification.

• Status: Certified DBA (Doing Business As)
• URL: https://www.bloomshift.com
• Read the [project debrief] here (coming 12/16)
• Brand affiliations: Lemlist, HubSpot, Sprocketeers.

#H4 Innovate Coalition — A nonprofit to dovetail the fundraising efforts of SUEGO

As I received funding across the startup programs from SUEGO, it became apparent that a non-profit might be more receptive to donor tax incentives.

• Status: Incorporated Non-Profit
• URL: https://innovatecoalition.org (broken site currently)
• Read the [project debrief] here (coming 12/16)

[P] The Partnered brands

These are collaborative brands that have been incubating over time and with other partners. These are ongoing across the year.

#P1 OrangeUP — An outsourced talent marketplace

Connecting LatAm (Colombia) talent with driven U.S. operators.

• Status: Incorporated C Corp.
• URL: https://orangeup.biz
• Affiliated brands: Techstars Startup Weekend, Founders Institute, Santander X.

#P2 CrowdWork — A cooperative focused on government grants

Building on-ramps for government contract opportunities.

• Status: Incorporated LCA
• URL: https://crowdwork.coop

#P3 ExI — Professional development for humans

Educational programming and events for mass professional development.

• Status: Launched
• URL: https://exponentialindividuals.io
• Brand affiliations: Boston ExO, OpenExO.

#P4 1Exponential — A festival and conference series

Building high-impact brand activations across the entrepreneurship sector.

• Status: Launched
• URL: https://1exponential.com
• Brand affiliations: OpenExO.

[B] The Icebox brands

These are other brands that we don’t have any time for in 2023.

#B1 BRIJX — Community development for young professionals

Educational materials around insights and experiences for mass benefit.

• Status: Launched
• URL: https://brijx.co

#B2 TradeTrip — An investor travel agency for LatAm

Travel agency services for investor relations across Latinoamérica.

• Status: Baking
• URL: https://tradetrip.org (broken site currently)

Resources

• Scaling Lean by Ash Maurya
• Measure What Matters by John Doerr
• 10 Pitch Slides by Guy Kawasaki
• SWOT Analysis [Mind Tools] [HubSpot]
• A Leaner Lean Canvas by Ash Maurya
• Top Startups & Scaleups advancing the 17 United Nations Sustainable Development Goals (SDGs) by StartUs Insights
• What Week Is It by Misja.com

This is a work in progress. Share any ideas on how to improve along the journey!

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Steven A. Rodríguez is the founder of SUEGO, creator of the channel BOGOWEEK, and rising author.