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📘Knowledge Drop: Decide and Negotiate Deal Terms

You've done your homework. You've completed deep dive due diligence on a startup that caught your eye. Now you need to decide if it's an investment you want to make, and if it is, is the pricing of the deal right for you. 

The Five Critical Steps After DD

1. Make the Actual Investment Decision

This is decision time, and you need to be ok with some uncomfortable truths. Most early-stage investments still go to zero. You'll never have perfect information; which means you can't wait around for certainty that will never come.

Ask yourself these questions:

  • Does it pass the due diligence text in terms of potential market size, founder strength, unit economics, etc.

  • Does it still make sense in my overall portfolio? You should think beyond this deal and consider how it fits with everything else you have or want to invest in.

  • Am I genuinely excited about the chances that this could be a winner, or just impressed with the concept?

If it's not a hell yes, it's probably a no. Anything in between maybe you trying to avoid making a decision.

2. Understand Price, Terms, and Cap Table

Deep dive DD tells you what the company is, but this step tells you what your money actually buys. Most angels lose money here even when they pick good companies, because they don't understand what they're actually getting for their investment.

Valuation Is About Ownership

Early-stage valuation is very subjective. Everyone's making up numbers based on comparables that don't really compare and traction that's too early to mean much. But ownership is rea,; it's the percentage of the company you own and that percentage determines whether you make life-changing money or just get your capital back via a modest return.

What you should care about:

  • How much do I really own?
    Not “what slice of this round did my check buy,” but “what slice of the entire company do I own after later rounds.”

  • What happens to that ownership later?
    If I own 0.5 percent today and I don’t have pro rata, future rounds will shrink me. After Seed and Series A, that 0.5 can easily turn into 0.3 or less.

  • Why is the price(valuation) this high?
    Is the valuation high because the company has real traction and momentum, or because the founder is overconfident and confusing hype with value?

If you’re under about 1%, don’t have pro rata rights and the next round is a ways out, there’s just not a lot of upside there even if things go right. In that case, either keep the check small or pass. Your money can work harder in deals with cleaner ownership and better economics.

SAFE Notes Are Where Angels Get Cooked

SAFEs are founder-friendly by design, and that's fine. What's not fine is angels not understanding what they signed. I've seen too many people write checks on SAFEs and then act shocked when they convert and realize they own way less than they thought they would.

You need to always check:

  • Valuation cap
    This is the highest price your SAFE can convert at. If the next round prices higher than the cap, you convert at the lower cap, which helps you. If the cap is already close to where the next round will price, it’s not really protecting you.

  • Discount
    This is a percent off the next round’s price, usually around 20%. It only matters if the valuation cap doesn’t apply.

  • MFN or not
    MFN means if later investors get better SAFE terms, you automatically get them too. Without it, newer investors can get a better deal than you.

  • Pre-money vs post-money SAFE
    Post-money SAFEs lock in your ownership. Pre-money SAFEs don’t and can get diluted by other SAFEs raised after yours. If it’s pre-money, you need to know how much SAFE money is already in.

  • SAFE stack
    Multiple SAFEs add up. A big SAFE stack means heavy dilution when the company finally prices a round.

If you can’t clearly explain what percentage you’ll own after Series A, you’re not investing, you’re guessing.

A common red flag is hearing, “Don’t worry, everyone’s on the same SAFE.” That often means there are a lot of SAFEs, the cap is high, or heavy dilution is coming. Strong founders are clear about their cap table. When founders dodge questions about SAFE terms, it’s usually for a reason.

Cap Table Health Matters More Than Pitch Quality

A great pitch plus an ugly cap table equals a bad investment. If the cap table is broken, you're not making money.

You're looking for:

  • Clean founder ownership: The founders should still own a meaningful chunk of the company. If they're already down to 40% combined at pre-seed, something went wrong early.

  • No weird early advisors with oversized equity: If someone got 5% for "introductions" in the first year, that's equity that should have gone to people who actually contribute ongoing value.

  • No Angels with special rights: You want a clean cap table where everyone's incentives point in the same direction.

  • Option pool not already bloated: If there's already a 20% option pool and they haven't hired anyone yet, that's a problem.

Black founders are often told "just take the money" and "terms don't matter at this stage." That's how talented founders end up trapped in bad structures that make it nearly impossible to raise a clean Series A later. As a Black angel, part of your value is not co-signing bad cap tables, even when you love the mission.

Pro Rata Rights: Real or Fake?

Everyone says "pro rata included," but is it actually real?

Questions to ask:

  • Is it contractual or just a side letter? If it's not in the actual SAFE or side letter, it doesn't exist.

  • Will I realistically be allowed to exercise it? If your pro rata in the next round is $5K and the minimum check is $25K, you're not really getting pro rata.

If you're writing a small check with no path to follow-on capital, your upside is capped early. That's fine sometimes, just be clear about it.

The Price vs Momentum Tradeoff

Sometimes you overpay on purpose, and that can be valid.

Valid reasons to “overpay”:

  • Elite founder with a proven track record

  • Competitive round with strong co-investors

  • Clear path to breakout traction

  • Strategic access or learning value

Bad reasons to overpay:

  • FOMO

  • Founder pressure

  • You don't want to "miss the wave"

Before you wire the funds, ask yourself: At this price, with these terms, I am comfortable with the potential outcome even if it takes 10 years.

The bottom line: Deep DD finds good companies, but price and terms decide whether you make money.

3. Consider Your Portfolio Context

No investment exists in isolation.

  • Sector concentration: If 60% of your portfolio is in fintech and you're looking at another fintech deal, you're probably taking on more correlated risk than you should.

  • Stage concentration: If everything you own is pre-seed with no revenue, you're going to have a very long time horizon before you see any liquidity.

  • Risk profile duplication: If you already own three companies betting on the same regulatory change, you don't need a fourth one.

Great angels think also in in context of their  portfolios

4. Document Your Belief

Before you wire, write a Belief memo for yourself. What has to go right? What would kill this company? You already know this info, this exercise is to cross T’s and dot I’s and double check your belief in the company and deal.

This document protects you later when emotions kick in and you're tempted to make decisions based on fear or FOMO rather than facts.

5. Close Clean and Build the Relationship

Once you commit, wire promptly and professionally. Help if asked and stay close enough to be informed.

Your reputation as an investor starts building the moment your check clears. Founders talk to each other, and if you're helpful, responsive, and low-drama, you'll start getting access to better deals.

Deals Open For Investment: UMI

UMI is tackling a massive women’s health gap: 2.7B women face hormonal disorders that mainstream healthcare doesn’t fix. They offer a 3 month, clinically proven, personalized AI powered program that delivers real results, not generic wellness.

They’ve already got 435 paying customers, 45.6k followers, 4,600 email leads, and $555k in revenue.

The founder has a 100k audience and a track record of helping women heal naturally.

Early results: 83 percent success rate, including cycle normalization and fibroid reduction from 4.8cm to 1.4cm.

🦄Deals On My Desk:

Ambient Intelligence - Replacing Wearables With Smart Rooms

Ambient Intelligence uses sensors placed in a room to keep people safe, without cameras or wearables. These sensors watch movement and patterns to spot danger early, like falls or health changes. It is like a “smart home + health monitor” that works in the background to protect seniors and patients.

Summary: Ambient Intelligence helps families, caregivers, and healthcare providers watch over people without asking them to wear devices or be on camera. The system tracks movement and behavior in real time and sends alerts when something looks wrong. This helps prevent falls, lowers medical costs, and gives families peace of mind.

The Backstory: The company was inspired by the founder’s grandmother, who lived with Alzheimer’s and later passed away after complications from the disease. Falls are a huge problem in healthcare. In the U.S., over $50 billion is spent each year on fall related injuries, and one serious fall can cost over $200,000. The team saw that wearables and cameras were uncomfortable, easy to forget, or raised privacy concerns. They built a better option that works quietly in the room instead.

Key Innovation: Ambient Intelligence replaces wearables with ambient sensors that live in the environment. The system detects falls, tracks daily patterns, and sends alerts without recording video. It is private, always on, and designed for senior care, assisted living, and remote patient monitoring.

Funding: The company is building toward scale with pilots, healthcare partners, and early customers. Comparable companies in fall detection have reached valuations near $190 million. Ambient Intelligence is focused on growing customers, reaching over $1M in ARR, and expanding across healthcare systems, senior living groups, and home care networks as the remote patient monitoring market grows rapidly toward a projected $100B by 2028.

❓Did You Know

Mayvenn, a Black-founded beauty tech company in the US, reached $100 million in annual revenue by building a marketplace that pays stylists directly.

Cheers,

Abdul

About Our Chairman

Hey Hey… I’m Abdul I’m the chairman of Ajo Angels and Shujaa Capital and I’m on a mission to introduce angel investing to 25,000 black folks over the next five years. I’m doing this with the goal of narrowing the racial wealth gap as well as trying to close the billion dollar funding gap for black founders.

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