August 28, 2025
After six months of being bootstrapped and hitting $150K ARR by myself, I'm about to take my first angel investment. And before you ask - no, it's not because I need the money.
This decision represents a fundamental shift in how I think about capital, growth, and the kind of people I want in my corner as I scale. It's also a masterclass in why the best investments are never just about money, and why waiting until you don't need investment is actually the perfect time to take it.
Here's the real story behind my decision to move from bootstrapped to strategically funded, and why the relationship-first approach to angel investment is the only way that makes sense.
Let me be clear about something: I didn't bootstrap by choice initially - I bootstrapped by necessity. I have four kids, a husband, two dogs, a house, and bills that don't care about my startup dreams. I needed to make sure that whatever I built could sustain my salary and support my family without relying on someone else's money to pay my bills.
That necessity became my identity. When I launched Theanna in February, I was in the top 18-20% of companies that hit $13K MRR in their first six months. I had to prove to myself, my family, and the market that this business could work before I ever considered taking outside money.
This foundation changes everything about how you approach investment. When you're not desperate for capital, you get to be selective. When your business is already working, investors become partners, not saviors.
Once you hit certain revenue milestones, your inbox explodes with investment inquiries. "Are you seeking investment?" "I'd like to invest in you." "Would you like to pitch?" It's flattering, exciting, and completely distracting if you let it be.
But here's what most founders miss: taking money from strangers who only see you as an investment opportunity is a recipe for misalignment. These investors don't know you as a person, a parent, or an entrepreneur with a vision beyond just returns. They see numbers on a spreadsheet.
I'm not someone who would go out and pitch a bunch of strangers asking for cash to fuel my business. That approach feels fundamentally wrong to me, and it sets up a transactional relationship when what you actually need is a partnership.
My approach to angel investment is simple: I only take money from people I know, trust, and who are in my corner whether or not I take their money. These are people who see me as a human being first and an investment opportunity second.
The person I'm bringing on as my first angel investor fits this criteria perfectly. Yes, it's a small check, but that's not the point. What matters is that I now have access to their knowledge, their experience, and their network. The capital is actually the smallest part of what they bring to the table.
This investor believes in me and the vision I want to accomplish. They understand my background, my motivation, and where I'm trying to take this company. That alignment is worth more than any amount of money from someone who doesn't really know what we're building.
Not all money is good money, and this is where so many founders make expensive mistakes. Good money comes with good experience, good networks, and good judgment. It comes from people who can help you navigate challenges you haven't faced yet.
When evaluating potential investors, I look at their background and experience first, money second. Can I call them anytime I need help? Do they have relevant experience in my industry or stage of company? Have they been where I'm trying to go?
The best angel investors become advisors, connectors, and champions for your business. They open doors, make introductions, and provide guidance based on real experience. The financial investment is just the entry fee to access everything else they bring.
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There's a perfect time to take angel investment, and it's not when you're desperate or pre-revenue. The best time is when your business is already working, you have proven traction, and you can be selective about who you partner with.
At $150K ARR, I don't need investment to survive. I need investment to accelerate and scale more strategically. That fundamental difference changes the entire dynamic of fundraising conversations.
When you're not desperate, you can focus on finding the right people rather than just any people with money. You can prioritize strategic value over valuation. You can build relationships instead of just pitching numbers.
The key to successful angel fundraising is starting with relationships, not pitch decks. The best angel investors are people who already know and believe in you before you ever ask for money.
This means being authentic about your journey, sharing your wins and challenges publicly, and building genuine connections with people in your industry. It means providing value to others before asking for anything in return.
The investors who reach out after seeing your success are different from the ones you cold-pitch when you're struggling. They're coming from a position of interest and respect rather than skepticism and due diligence.
Taking angel investment isn't about needing money - it's about choosing the right partners for the next phase of your journey. When you build a solid foundation first and approach fundraising from a position of strength, you get to be selective about who joins your mission.
The relationship-first approach takes longer and requires more intentionality, but it results in partnerships that actually accelerate your business rather than just funding it. The best investments are never transactional - they're deeply relational.
If you're considering angel investment, start by proving your business works first. Then focus on building genuine relationships with people whose experience and networks align with where you're trying to go. The money will follow the relationships, not the other way around.
Build something that works, be authentic about your journey, and the right angels will find you when you're ready for them.
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