Training Library

Learn to execute.

Fourteen playbooks and three skill tracks. No filler. Just the frameworks that move the needle — written in Ledger's voice for founders who are done with inspiration and ready to build.

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Playbooks 14 execution guides
Sales
Cold to Closed
Getting your first 10 customers from zero.
You're waiting for referrals or inbound. That's not a strategy at $0. Cold outreach is a numbers game with a quality filter. Volume times relevance equals conversations.
  • 01Target 50. List 50 people who have the problem you solve. Not businesses. People. A name and a reason for each.
  • 02The one-line hook. "I help [specific person] do [specific outcome] in [specific timeframe]. Are you working on this?" No deck. No PDF.
  • 03Follow up once. 5 business days later. One sentence: "Did this land in a bad week?" Then stop.
  • 04The close question. "Does it make sense to spend 20 minutes this week to see if this fits?" Never ask for a sale on the first contact.
  • 05Score and track. After each call, score the lead 1-3. 1 = not a fit, 2 = possible, 3 = live. Track this or repeat the same mistakes.
Common Mistake
Spending 80% of your time on the message and 20% on volume. A decent message sent to 50 people beats a perfect message sent to 5.
Drill
Write your one-line hook right now. Read it aloud. If it sounds like a LinkedIn post, rewrite it.
Sales
Price Without Apology
Setting and holding your rate in any conversation.
Undercharging doesn't close deals — it attracts bad clients. Price is positioning. A low price signals low confidence. A held price signals conviction.
  • 01Set your number. Calculate your minimum viable rate, then add 30%. That's your price. Not your opening, your price.
  • 02State it flat. "It's $X." Full stop. No "approximately", no "starting at". Say the number and be quiet.
  • 03Handle pushback. "That's more than I expected." Don't apologize. Ask: "What were you working with?" Then listen.
  • 04The discount test. Before you discount, ask: "Would I work with this person at full price if they paid it?" If no, don't discount — exit.
  • 05Hold and wait. If they push back and you hold, 40% come back and accept. The other 60% were never your clients.
Common Mistake
Justifying your price unprompted. The moment you explain why you're worth it, you've started negotiating against yourself.
Drill
Say your rate out loud to a wall, 10 times. Each time, stop talking immediately after the number. No qualifiers.
Ops
The Weekly Sprint
The 7-day execution framework that replaces vague goals.
You set goals monthly but make decisions daily. The gap between those timescales is where execution dies. Sprint in 7-day cycles — long enough to move, short enough to course-correct.
  • MONThe Single Bet. Pick one outcome that makes the week a win. Not a task — an outcome. "Signed first client," not "sent emails."
  • DAILYThe 15-Minute Brief. Answer three: What's the one thing today? What will try to pull me off it? What does done look like by 5pm?
  • WEDMid-Week Check. On track for Monday's outcome? Yes → keep going. No → is the outcome still right, or do you adjust?
  • FRIHonest Score. Score the week 1-10. Don't score effort. Score output. "Did the outcome happen?" is the only question.
  • RULEPattern Break. Two weeks under 6 in a row means something structural is wrong. Find it before starting the next sprint.
Common Mistake
Tracking activity instead of outcomes. Sending 40 emails is activity. Booking 3 calls is an outcome. Only outcomes count.
Drill
Define your Monday outcome for next week right now. One sentence, one outcome. Write it somewhere you'll see it every morning.
Ops
The Constraint Method
Find and eliminate the one thing blocking your growth.
In any system, there is always exactly one constraint. Fix it and the whole system speeds up. Everything else is noise. Most founders are optimizing the wrong step.
  • 01Map the flow. Draw your revenue path from "stranger hears about you" to "money in account." Mark every step. Do it on paper.
  • 02Find the pile-up. Where does work sit the longest? Where do leads stall? Where do you spend the most time for the least output?
  • 03The two questions. "If this step went 2x faster, would revenue grow?" and "If it broke, would revenue stop?" Yes to both = your constraint.
  • 04Eliminate before optimizing. Before improving the constraint, ask if it needs to exist. Automating a broken step makes broken things faster.
  • 05Exploit first. Squeeze 30-40% more from the constraint before adding resources. The capacity is usually already there.
Common Mistake
Optimizing the steps before your constraint. If closing is the bottleneck, better lead gen just creates more pipeline you can't handle.
Drill
Draw your revenue flow in 10 minutes. Circle the constraint. Write one thing you'd do this week to widen it.
Sales
The Objection Stack
Every sales objection, reframed and answered.
Objections aren't rejection — they're unresolved concern. Your job is to surface what's underneath. Respond with a question before a statement, every time.
  • 01"I need to think about it." Translation: I'm not convinced and won't say why. Response: "Totally fair. What part is giving you the most pause?" Then stop talking.
  • 02"It's not in the budget." Translation: I don't see enough value. Response: "Is it the total number, the timing, or the perceived return?" Address only what they name.
  • 03"Send me more info." Translation: Not urgent. Response: "What specifically would help you move forward after reading it?" No answer = the info won't help.
  • 04"We already have something." Translation: Convince me to switch. Response: "What would need to be true about what I'm offering for it to be worth the change?" Let them set the bar.
  • 05"I need to talk to my partner." Translation: I want a co-decision maker. Response: "Would a 20-minute call with them together make sense?" Usually yes.
Common Mistake
Responding to objections with statements. Statements put people on defense. Questions make them think. Always ask before you answer.
Drill
Write out the last 3 objections you heard. Now write the question you should have asked in response to each.
Finance
The Pitch Map
Structure any pitch for any room.
A pitch isn't a presentation — it's a transfer of conviction. Your job is to make someone else believe what you believe. Most pitches fail because the structure is wrong for the audience, not because the idea is bad.
  • TESTThe 3-Sentence Test. (1) Who is suffering and why. (2) What you do and how. (3) Why now and why you. If you can't pass this, the pitch isn't ready.
  • INVFor investors. Problem size → your insight → solution → early evidence → ask. Every element earns the next one.
  • CUSTFor customers. "Right now you deal with X. That costs you Y. We fix it in Z. Here's proof. Ready to start?" Simple. No jargon.
  • PARTFor partners. State what they get first. Then what you get. Lead with your need and you lose.
  • EDGEThe killer detail. One specific, verifiable, unexpected fact that makes your insight undeniable. Not a trend report. Something you lived.
Common Mistake
Spending 80% on the product and 20% on the problem. Investors fund solutions to large problems. If they don't feel the problem, they won't believe in the solution.
Drill
Write your 3-sentence test answer now. Read it to someone who doesn't know your business. If they're confused, it's not their fault — rewrite.
Ops
Hire or Don't
The decision framework for your first hire.
Founders hire too early when scared and too late when desperate. Both are expensive. Your first hire should multiply your output — not replace your avoidance.
  • 01The gate test. Is this role blocking revenue today? Could a contractor or tool do this? Do I have 90 days of salary plus 30% buffer? All three must be yes.
  • 02Who first. Almost never a salesperson. Almost always the person who does what you do second-best — usually ops or delivery.
  • 03Week-one evaluation. Give one real project, one real deadline, one real constraint. How they handle ambiguity in week one predicts crisis response in month six.
  • 04The exit trigger. Coached the same behavior twice. Documented it once. Still wrong. The third time is an exit conversation — not a coaching session.
  • 05The non-obvious rule. The best early hire has operated in chaos before, not someone comfortable with structure. Chaos experience transfers.
Common Mistake
Hiring someone to solve a systems problem. If work keeps falling through the cracks, a new person will also fall through the cracks. Fix the system first.
Drill
Write the exact role you'd hire right now. Then ask: does this person stop something from breaking, or grow something that's working? If it's the first — build a system instead.
Finance
Capital Ready
What investors actually look for — and what they don't.
Most founders pitch what they've built. Investors fund what they believe can happen. They're making a 7-10 year bet on your ability to navigate uncertainty — not buying your product.
  • 01What they actually look for. Evidence you know the customer better than anyone. A model that can get big. Early proof the machine works at small scale. A founder who knows what they don't know.
  • 02Pre-seed metrics that matter. Conversations with real customers. Any paid transactions. Retention if you have a product. Response rates. These are signal — deck quality is not.
  • 03The narrative trap. The pitch isn't about convincing. It's demonstrating you've already thought through the hard questions. If you need to be convinced of your own business, they won't believe it either.
  • 04What kills deals. Valuation anchored on ambition, not comparables. "We're going after everyone." A team that can't explain why they specifically win.
  • 05The ask. Know exactly how much and exactly what it funds. "$500K. $300K engineering, $150K customer acquisition, $50K ops. We'll have X by month 12." Precision signals execution confidence.
Common Mistake
Waiting until you have a polished deck. The founders who raise earliest have customer evidence, not design skills. Get conversations before slides.
Drill
Answer out loud: "Why are you the person to build this, and why is now the moment?" If your answer is vague, the investor will move on.
Sales
The Cold Email Engine
50 targeted emails a day. Inbox to booked.
Ops
Negotiation Fundamentals
Never leave value on the table again.
Ops
The 90-Day Revenue Plan
A quarter-by-quarter execution blueprint.
Sales
Referral Architecture
Engineer word-of-mouth instead of waiting for it.
Finance
Read a P&L
Know your numbers cold before an investor does.
Ops
The Founder's Calendar
Time blocking for high-output weeks.
Skill Tracks 3 progressive learning paths
Close More Deals
5 sessions · Sales
S1 The Sales Mindset Reset
Most people approach sales as persuasion. It is actually investigation. Your job is not to convince — it is to find out whether there is a fit, and if there is, make the fit obvious. Persuasion creates clients who resent you. Investigation creates clients who refer you. The shift: replace "here's why you should buy" with "here's what I'd need to know to help you." Notice what changes in the conversation.
Exercise
On your next 3 sales conversations, commit to asking 2 questions before making any statement about your product. Track whether conversations last longer.
S2 The Qualification Filter
Not every lead is worth your time. The fastest way to close more is to stop chasing deals that won't close. Your qualification filter has 4 gates: (1) Do they have the problem you solve? (2) Do they feel the urgency? (3) Do they have budget, or authority to find it? (4) Are they the decision-maker? If they fail any gate, be honest about fit early. A "no" in week one is worth more than a "no" in week eight.
Exercise
Score every active deal in your pipeline on all 4 gates right now. Any deal with two or more fails is not a deal — it's a distraction.
S3 The Objection Playbook
Objections tell you exactly what to address. Treating them as doors closing is the mistake — they are windows opening. The three you will face most: "Too expensive" (they don't see enough value yet), "Need to think" (something is unresolved), "Not the right time" (urgency hasn't landed). For each one, your response is a question, not an answer. "What part is the sticking point?" surfaces the real issue every time. Do not respond with a defense — respond with curiosity.
Exercise
Write out your top 3 objections. For each one, write the single question you will ask in response before you say anything else.
S4 The Follow-Up System
80% of deals close after the 5th touchpoint. Most founders give up after 2. The follow-up cadence: Day 1 — recap and next step. Day 5 — one-line check-in. Day 14 — new angle or new information. Day 30 — "Is this still on your radar?" Quarterly after that. Never apologize for following up. You are offering something valuable — follow-up is a service, not a nuisance. The founder who stays visible wins the deal the one who gave up deserved.
Exercise
Set up a simple tracking system — even a spreadsheet — with every active deal and a follow-up date. Block 30 minutes each Friday to action it.
S5 Closing on the First Call
The best close is the natural outcome of a great discovery conversation. If you have qualified correctly and addressed the real concern, the close is just logistics. The one-call close works when three conditions exist: the problem is urgent, the budget exists, and you are speaking to the decision-maker. When all three are true, ask: "Based on what you have told me, this sounds like a strong fit. What would need to happen for you to get started this week?" Then be quiet. The next person to speak buys.
Exercise
On your next qualified call, if all three conditions are met, commit to asking for the business. Write the exact sentence you will say, and practice it before the call.
Build Your System
4 sessions · Operations
S1 Why You're the Bottleneck
Every founder is a bottleneck at some stage. The question is whether you have accepted it or are still pretending you can manually scale. Signs you are the bottleneck: you are copied on every decision, nothing ships when you are unavailable, new people ask you the same questions repeatedly. This is a structural problem, not a workload problem. Working harder will not fix it. Designing your way out will. The goal of this track is to make your business able to operate one level better without you in every decision.
Exercise
Track every interruption for two days. Categorize each one: decision-making, information-finding, task-doing, problem-solving. The top category is your first system to build.
S2 Mapping Your Operations
You cannot fix what you have not drawn. Map every repeatable process in your business: how a lead becomes a client, how a client gets delivered to, how an invoice gets created and paid. Use a simple flowchart. At each step, ask: who does this, where does the information live, and what does failure look like? Most businesses have 3-5 processes that touch 80% of their revenue. Those are your priority. Once you can see the whole map, the gaps become obvious — and fixable.
Exercise
Map your top revenue-generating process end to end. Count the total steps. Circle every step that only you can currently do. That list is your system-building backlog.
S3 The First Hire Framework
A system hire is different from a growth hire. A system hire takes a process completely off your plate. A growth hire expands something that is already working. Make system hires first. For your first system hire: document the process completely before posting the role, hire someone who has done the specific thing before rather than a generalist, and give them 90 days with a performance definition that is clear enough to be unambiguous. The right hire makes you feel free. The wrong one makes you feel watched.
Exercise
Write one complete process document this week — instructions clear enough that someone else could run it on day one with no additional context from you.
S4 Scaling Without Breaking
Scale breaks three things reliably: communication (too many people, too little context), quality (output variability grows with volume), and culture (values dilute when hiring fast). The fix is not to slow down — it is to build guardrails before you need them. Communication: weekly team brief, one source of truth for decisions. Quality: define what "done" looks like before starting any deliverable. Culture: hire for judgment first, skill second. The people who join at 10 will define who joins at 50 — they carry the standard or lower it.
Exercise
Define "done" for your most common deliverable in one clear paragraph. Share it with your team and see how differently they interpret it compared to your definition.
Think Like an Investor
4 sessions · Finance
S1 How Capital Actually Works
Most founders think of funding as a milestone. Investors think of it as a wager. You are not receiving validation — you are entering a contract where someone bets on your ability to return 10x or more. Understanding this changes everything: who you approach, how you pitch, how you structure the deal, and how you behave as a CEO afterward. Most startups that fail do not run out of ideas — they run out of capital because they did not understand how capital decisions compound. Every dollar you raise has a cost: equity, expectation, and obligation. Raise intentionally.
Exercise
Calculate your current burn rate. How many months of runway do you have? At what point do you need to have the next raise closed — and when does that mean you need to start?
S2 What Your Metrics Say About You
Before you pitch, know your numbers cold — not because investors will quiz you, but because how you talk about your metrics reveals how you think. If you know your CAC, LTV, churn, and gross margin from memory, you signal operational depth. If you don't, investors assume you are not running a tight ship. The metrics that matter most depend on your stage. Pre-seed: leading indicators — conversations, pilots, letters of intent. Seed: early retention and unit economics. Series A: repeatable revenue growth and a clear path to profitability.
Exercise
Write down your 5 key metrics from memory right now, without looking anything up. Which ones can you not fill in? Those gaps are the ones to close before any investor conversation.
S3 The Narrative Framework
Data does not raise money. Narrative supported by data does. Your narrative has four components: the insight (what you see that others do not, and why now), the evidence (proof the insight is real — even thin proof matters), the model (how you turn the insight into a scalable business), and the team (why you specifically are the ones who win). Most founders lead with the product. The best pitches lead with the insight. If the investor agrees with your insight, the product becomes obvious. Make them see the world the way you see it first.
Exercise
Write your insight in one sentence. It should be a specific, non-obvious observation about the world that most people would initially push back on — until you explain it.
S4 The Term Sheet Conversation
Getting a term sheet is the beginning of a new process, not the end of one. The terms you accept shape every future decision. The ones that matter most: valuation (your dilution today affects your leverage later), board composition (who controls decisions when things get hard), pro-rata rights (which investors can follow in future rounds), and liquidation preferences (who gets paid first in an exit). You do not need to be a lawyer. You do need to understand what you are agreeing to. Choose your negotiation battles carefully — fighting everything signals you are difficult to work with.
Exercise
Look up "liquidation preference" and "pro-rata rights." Write a plain-English explanation of each in your own words, as if explaining to a smart friend with no finance background.