2025 Reflection
What has the year been?
I have been learning how to find my own personal statement in the business world. I was nudged toward the business side because I believed a product nobody uses is not a product worth building. I was mistaken about how tidy that belief is in practice—and what it costs to make something people actually use.
I used to assume technical people were second to “the business person,” and I wondered why I should not be the person out front. I was wrong again. The person in front can be the face of the moment, but it is the technical work behind the scenes that makes the moment possible—by building products people use and delivering value for real desires and problems.
A note to myself at this stage of the company: do not lose sight of that. We keep looking at lists like this:
- Parag Agrawal — former CEO of Twitter
- Eric Schmidt — former CEO of Google
- Andy Jassy — CEO of Amazon
- Satya Nadella — CEO and Chairman of Microsoft
It is tempting to think, as a technical person, that it is simply my turn to “step up.” I have been wrong a third time. These are not overnight moves, and they are not the story of a five-year-old startup. They are transitions built on decades of business model and hustle.
Even so, here are some lessons I am carrying about how a technical person can operate in the business world.
1. Speak their language
You go to a new city with its own language; you learn it if you want to belong.
Speak the language of business: strategy, impact, strategic value, KPIs, politics, agendas. Not a simple binary of ones and zeros; not only right and wrong. Often it is about what you want to achieve and what you are willing to do to get there.
Learn to meet people where they perceive the need—otherwise they may not see a reason to listen.
2. Build systems that scale beyond yourself
At this pivot in my startup, I am stretched across concurrent work that all wants attention in the same short window. I am no longer only an individual contributor without cost: opportunity cost shows up when I am absent from other roles—managing account management, or QA, or whatever else needs a lead.
Even when I push to stay an individual contributor, sixteen-hour days return, and then incentives and sustainability come into question.
What system do I need so good work keeps flowing without burning me out? What kind of systems thinking do I need to pass to the team so they can own their part of the machine?
These are not fluffy ideas I once attributed to “business people” when I was only a software engineer. Processes matter so people inside the system can find purpose and role in the bigger picture.
A good system empowers the parts of the whole. Sometimes those parts do not even see how they succeed—and, as I have done, they wrongly credit individual heroics. You do not hear the chess piece bragging about the knight while the bishop lines up the king. We are pieces in a larger game; pride misreads the board.
That surfaces why this line lands so hard:
“Pride goes before destruction, and a haughty spirit before a fall.” (Proverbs 16:18)
When pride clouds judgment, we attribute success to the wrong causes—often ourselves—and we lose sight of what actually moved us forward.
Systems thinkers and builders are often unsung. To leaders reading this: this attribution is for you.
You are doing well when your people feel empowered and rise to what is in front of them. Like good parents stepping back so a child can own a win—and, prayerfully, grow confidence for what comes next—you multiply impact in ways people do not always name.
Keep your head and ego grounded. Leadership, for me, is to serve, not to be served.
Below are growth areas I reflected on through 2025. I am consolidating them for my future self, and for anyone else in a startup who needs the reminder: we are all works in progress.
Talking to senior people of influence
- Connect your beliefs to their vision for their institutions.
- Present yourself as a contributor.
- Position yourself as a learner—what attributes and competencies should someone like me, aiming at impact in education, grow while still learning to lead?
- Be able to explain why you asked for the meeting.
- Be genuine; build rapport. Understand vision and strategy alignment.
- Part of my own mission statement belongs in that frame.
Talking to senior people in a sales process
- Do not fight ego with ego—answer and engage on their terms.
- Take their ideas seriously at the business level, not only as implementation detail. Broad strokes matter here.
- Talk KPIs and numbers versus the percentage of cost savings they can achieve.
- They are often thinking about processes and systems their operators will run.
- Find their KPIs and alignment high enough, and they may link to national agenda.
Talking to senior people as a peer
- Create psychological safety.
- Enjoy ordinary life in the conversation.
- Ask what they do first; acknowledge their impact.
- Treat them as friends, not only titles.
- They need rest and family time, too.
Leading the team
- Push for decisions that are clear and high quality—test and assess quality fairly.
- Step in with visible support; steer direction while the team handles execution.
- Do not bypass your lead—empower the lead to finish the job.
- A written warning is not “giving chance” twice; treat it as the serious step it is.
- Do not tolerate B-grade work.
- Give clear guidance for low-TRM situations, with language that helps people make sense of the task. Categorise task types when you give low-TRM instructions.
- Separate feedback types: appreciation, coaching, evaluation.
- Keep strategic alignment through active management.
- Hold safe spaces; learn how to guide them on TRM. Be intentional with documentation for low-TRM tasks.
- Push for better, more effective huddles.
- Bring the team back to shared mental models.
- Stay humble enough to ask for feedback—strong players will answer.
- Everyone matters; treat them with grace, as stewards of the work.
Team process
- How do we set up the process so quality is visible and upheld?
- Put a KPI where everyone can see it.
Talking to VCs
- Lead with vision.
- Know your asset class and how they see you.
- VC: often 50–100x in 8–10 years; rough check sizes like ~1M for 10–12% (illustrative).
- Family office: often 3–5x in a few years; smaller percentages; possible PE-style exits.
- Talk variable cost: what does it take to serve the clients that justify the scale story? Margin targets (for example, 40%+) matter in how you frame it.
- Do not pitch like a pure operator; show them the obvious opportunity they might miss.
- They may not be domain experts in your space, but they are strong at pattern recognition: big market, clear problem, fast growth, a team that wins.
- Your job is not to over-educate or over-defend.
- A simple spine helps: problem (why now), solution, market, traction, business model, team, vision and ask.
Team management
- Be firm on quality; use a first written warning for what it is meant to do.
- A-players are rare; cherish pockets where they cluster.
- I am still learning how to grow team leads into A-players—and how to lead through a lead who is not yet an A-player.
- Diagnose before you judge; if someone over-communicates, affirm more often.
- Give productive feedback, especially with experienced hires.
Sales
- Cold calling—still working on booking the meeting.
- Structure email with more discipline.
- Stay a problem finder.
- Turn latent need into active need.
- Follow a reminder structure, but learn when to pull back if the thread is off track.
- Sales material matters.
- Track email opens (e.g. Shortwave, MailSuite).
- Track assets and alignment.
- Get clearer on pricing conversations.
- Find the champion—you will see them in output and outcomes.
Events
- Drive conversations at events.
- Follow up after.
Founder friends
- Keep founder friends close.
- Show up for the community (777).
- Many people struggle when their technical co-founder is not in the room.
Founder learning
- Juggle sales, product, and project without dropping the story.
- Move the team while holding the standard.
CTO learning
- Do not walk away from this role lightly.
- If you need air cover, someone has to step in—you are not “released” from ownership by default.
Christian learning
- We bring God glory as Christian entrepreneurs when we build something strong and true.
- Consistency with a through-line.
- Layer music when it helps the vibe.
Hiring
- Video can help attract the right people.
- If candidates miss the bar, revisit the job description.
- Hiring “dev house” engineers needs a different assessment than a product team hire.
Visibility: room for improvement
- Know the people in the landscape (for the next few years, many names I hear are Chinese).
- Conversations for partnership.
- Conversations for business.
- Alignment checks with the other party.
- Conversations for VC.
- Career-prep frameworks in the market.
- Go-to-market events.
- How to get unstuck.
- How to work with dev houses and stay resourceful in crunch time.
Technical lead / engineer
- A hard year.
- Architecture was not vetted the way it should have been.
- Contractors rotate; long-term ownership of the codebase suffered.
- Clean up while you still can.
- Track tech debt with owners and dates.
- Keep innovating so compounding shows up.
- A strong product saves the company pain.
- Do not let go of solution architecture.
Engineers
- Handle technical debt actively—it cannot vanish overnight.
- Pace debt paydown on codebases others built.
11 Nov
Learning to lead on tech and project timing: hiring for the role, teaching and bridging trust gaps, supporting other leaders. Grateful for a friend through the stress, and for being a husband who can share the load.
9 Dec
Learning how to recover from a technical mistake.