Entrepreneurship Success Guide

The day I took a 3 AM business call from New Zealand, I knew I'd failed. My girlfriend looked at me and said: "You don't own a business. Your business owns you." She was right. I'd built a successful company but forgot to build myself out of it. The best founders do one thing brilliantly: they build systems. Here's the framework that changed everything: 1. The $5,000 Hour Rule I audit my week every Sunday with one question: How many hours were actually worth $5,000? $5,000 hour tasks: • Vision setting • Hiring A-players • Strategic decisions • High-level partnerships $10 hour tasks: • Inbox zero • Editing videos • Micromanaging • Managing Slack threads Then I delegate, automate, or eliminate everything else. 2. The 4 Core Systems Most founders get lost in complexity. I focus on four systems: 1. Vision Clarity System Where are we going in 3 years? Everyone needs to know. 2. Role Definition System Who owns what? No overlap. No confusion. 3. Communication Rhythm System How do we stay aligned without endless meetings? 4. Decision Framework System How do we choose fast without me being involved? Build these four first. Everything else is noise. 3. Hire Solutions, Not Problems The worst hires ask: "Matt, what should I do?" The best hires say: "Here's the problem, here are 3 solutions, here's my recommendation." This one shift let me go from 16-hour days to 4-hour days. 4. The Rule of Three Anything I do more than 3 times gets documented. Loom plus Google Docs create playbooks so detailed a high schooler could follow them. Client onboarding? Documented. Team meetings? Documented. Customer complaints? Documented. If it's not documented, it doesn't exist in my company. 5. The Freedom Test Here's how you know your systems work: Can you disappear for 4 weeks without your business falling apart? I recently spent 3 weeks in the Dolomites with zero business calls. My team made every decision. Revenue grew 12%. Customers were happier. That's what real systems look like. Most founders build themselves into their business. Smart founders build themselves out of it. __ Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Ready to learn how to remove yourself from operations? Get the complete system that helps founders multiply profits while working less: https://lnkd.in/eQ4RCByh

For my first 16 years in tech sales, I averaged 240K/year. In my last 4 years, I averaged 720K/year. I did this by using an approach I call Yo-yo selling: 🪀 It’s how you win large, complex enterprise deals by building credibility with senior executives at the beginning of a sales cycle. This will save you months of spending time with mid or lower level Directors on a deal cycle, only to have your deal stall because it's not a priority for Executives. Here’s the concept: You start at the top, get senior level sponsorship for a deep discovery, drop down into the business, then bounce back up with a report of findings. This is the process I've used for nearly every 7-figure deal I've ever closed. Step 0: Research before outreach Before asking for time, I do deep strategic research. Earnings calls. Investor decks. Press releases. Executive interviews. I also spend time talking to their team to see if the problem that I solve exists in their company. Using that research, I build a Point of View that connects their top business goals to real execution gaps. This earns executive time. Today, AI tools like ChatGPT make this easier than ever. What used to take hours now takes minutes. If you skip this step, you lose your edge. Step 1: Prospect to the top and gain their sponsorship to engage Lead with your POV. The key is to teach them something new about their business which they aren't already aware of, and show them how it's putting their highest level goals at risk. If they lean in, offer up a deep discovery with your team and their team. Lock in a date to come back for a readout. Have them assign a project manager to help you coordinate Step 2: Drop down Once you have executive sponsorship, meet with their team. The key is to have the Exec sponsor send out a note to their team explaining what it's for. This will keep the assessment moving forward. Study workflows. Capture friction. Collect quotes. Do not pitch. Just listen. Step 3: Bounce back up Bring it all together in an executive summary. Show how their vision connects directly to what’s broken below. Present a focused business case. Build a custom demo. Create a roadmap and implementation plan. That’s where deals close. Real example from my career At Berkshire Hathaway HomeServices, we were told “no” on a point solution. Instead of walking away, I stepped back and asked what the company really needed. After deep research, I re-engaged the COO with a transformation POV centered on the experience of 50,000+ agents. The result was one of the largest new logo deals in Salesforce history. But Yo-yo selling alone isn’t enough. Because it's hard to execute and takes patience. Top performers also master their mindset, habits, and discipline. That’s why I put together a free masterclass for sellers who want to break into the top 1 percent. 👉 Watch the free training here: https://lnkd.in/eWD8mTqH If you’re serious about enterprise sales, this will change how you sell.

I grossed $81,109 in Q2 as a part-time creator. no management or viral moment. Just consistent systems, repeatable offers, and a clear message that attracts the right brands. Here’s where the revenue came from: ✔️ Sponsored Content (67%) ✔️ Brand Partnerships (14%) ✔️ Speaking Engagements (9%) ✔️ Advising (7%) ✔️ Digital Products (2%) ✔️ Newsletter Ads (1%) I share this because 3 years ago when I started I didn’t know how to charge more than $500 for anything. I thought I needed a huge audience and representation. But all I needed was a strategy. Here’s what worked for me: 1. Revenue follows trust and trust is built in public. From day one, I shared my ideas, gave away value for free, and stayed consistent. That's still my number one focus today. 2. Price everything in advance. Know your rates before they ask. It removes emotion and speeds up decisions. 3. Save a counter-offer email template. A calm, clear response helps you push back without burning bridges. 4. Treat your brand like a business. The newsletter, brand deals, advisory work, and speaking gigs aren’t side hustles. They’re business lines and I have a plan to grow each. 5. Be selective. Growth isn’t about saying yes to more. It’s about saying yes to the right things, the ones that compound your credibility, audience, and income. 🧠 If you’re a creator-entrepreneur who wants help, I break this down weekly in my newsletter Content to Commas 📩 Join the community → https://lnkd.in/g9EGuyRa

Thinking of entering defence? Good. But read this first, or get crushed. You’re not building a startup. You’re entering a war zone with Excel sheets instead of bullets. And here’s the first landmine: Defence doesn’t care about you. Not until you matter. And by the time you matter, it might be too late. So here’s your brutal, field-tested playbook 👇 🔻 1. Run a Dual-Use Strategy or Die Trying Don’t “pivot into defence.” Don’t “add military as a target customer.” Build something with teeth in both markets — or you’ll starve while waiting 24 months for a MoD reply. Dual-use = survival. Omni-use = dominance. 🔻 2. Your Actual Competitor? Paper. You're not fighting primes. You're fighting outdated workflows, 94-page requirement PDFs, and evaluation committees who’ve never used the tech. You’re not selling innovation. You’re selling the idea that innovation should exist. 🔻 3. Never Ask for Feedback — Ask for Budget Lines Everyone will “love” what you’re doing. They’ll invite you to panels, workshops, incubators. None of that pays your team. Ask: “Which budget pays for this in Q4?” If they can’t answer, walk. 🔻 4. Find a Uniformed Insider, or You’re Screwed No matter how good your pitch is, you need a believer inside the system. Someone who speaks procurement and can say, “This solves my mission.” Without that: enjoy limbo. 🔻 5. If You’re Not Testable, You’re Not Real Defence doesn’t buy PowerPoints. You need a testable MVP fast. No test = no traction. No traction = no procurement route. No route = you're just theatre. 🔻 6. The First Deal Will Break You It’s slow. It’s painful. It’ll take months, maybe years. But once you break the wall once, you become “pre-approved.” Then the real business begins. 🔻 7. Ignore All of This If You're Building Slideware This advice is only for builders. For founders ready to live in uncertainty, raise from niche VCs, and get 50 no’s before one test flight. If you're not all-in: stay in SaaS. This is the most misunderstood opportunity of our time. Europe is waking up. The U.S. is doubling down. And the next industrial revolution will wear camouflage. Startups who learn the terrain will dominate. Speed. Testability. Dual-use. Insider access. That’s your survival kit. Use it. #DefenceStartups #DualUse #InnovationInDefence #OmniUse #MilitaryTech #InsiderIntel #BoldMovesOnly #WakeUpEurope

80k orders into TikTok Shop, here's what I've been surprised to learn.   1. Samples have only driven 7% of our TikTok Shop sales.   40% of orders come from product card. Of the 60% are driven by videos.   Product card: Customers organically finding our product on TikTok. These orders aren't charged commission. 🤌   Video: Most video sales are from affiliates who already have our product or they show our product image. On samples sent to affiliates, we get a 3 ROAS. Factoring halo sales on Amazon & DTC, it's a 6 ROAS (more in point 3). Half of our revenue from samples are from one affiliate. If you remove them, omni-channel ROAS is closer to a 3.   Product drop video posts from our own account can really work. Without commission owed, we can afford to put ad spend behind them.   2. TikTok Shop sales haven’t driven meaningful Simple Modern TikTok followers.   In the 6 months we sold 80k units on TikTok Shop, Simple Modern's TikTok follower count grew less than the previous 6 months.   Surprising to me considering we've driven 186m product impressions.   3. Over 100% halo effect between Amazon and Website.   When a product has a successful video driving TikTok Shop revenue, the bump on other eComm channels is clear. Typically we see more sales driven by TikTok videos on Amazon + DTC than TikTok Shop.   Customer trust is higher on Amazon and brand's websites.   The real magic is when TikTok videos goose Amazon listing placement permanently.   4. Revenue/video is flat once affiliates have more than 50k followers.   Followers: Revenue/video 0-1K: $13 1k-5k: $25 5k-10k: $40 10k-50k: $75 50+: $100   Affiliates with 50k followers have performed the same as 1m follower accounts. We have not engaged multi-million follower accounts with highly engaged audiences (celebrities).   5. Amazon best sellers don't drive our TikTok Shop business.   Products that have worked have had at least one of these qualities:  - Interesting  - New  - Relevant to culture or season  - Niche cult following (ex: Winnie the Pooh)   Our best sellers in retail typically don't have these qualities. These factors make inventory planning for TikTok Shop challenging.   6. Affiliates asking for 4+ samples are taking advantage of you.   We've sent 51 affiliates 4+ samples. Only one generated a sale.   13% of our total samples have been sent to grifters. 🙃   ************* TikTok Shop is a uniquely valuable channel since it's also a marketing engine.   It has required a different strategy from us and has been fun to learn.   I'd love to read what others have learned in the comments.

Everyone says, “Do internships to get experience.” But most roles didn’t even teach anything useful. So here’s what you can do to use your finance skills to gain hands-on experience and make money while doing it. 📌Stock Analysis for Newsletters If you know how to study stocks and market trends, you can work with finance newsletters or websites. Many platforms need people to write about stock recommendations or market insights. You can either join an existing newsletter as a freelance analyst or start your own using platforms like Substack. If your advice is useful, people might even pay for your premium insights. 📌Finance Content Creation If you enjoy making videos or posts, you can share finance tips onlinelike how to save money, invest, or manage personal finance. 📌Freelance Financial Modeling If you're good with Excel and financial projections, startups and businesses may need your help. They use financial models to plan growth or raise funding. You can charge per project and work with multiple companies as a freelancergreat for making good money on the side. 📌Bookkeeping for Startups Yes, bookkeeping sounds boringbut it's a solid side income. Many small companies don’t have in-house accountants and are happy to hire freelancers. If you know basic accounting or tools like Tally, you can manage their books, help file GST/TDS returns, and even assist during audits. 📌Personal Finance Coaching If you’re good at explaining saving, investing, or budgeting, you can offer 1-on-1 coaching sessions. Many people want help but don’t know whom to ask. You don’t need to be a certified advisorjust offer practical, honest guidance. Start with friends or social media, and build from there. 📌Tax Filing Services Every year during tax season, people need help filing taxes. If you understand the process, you can help individuals or small business ownerseven if you're not a CA. You can charge per filing or offer quarterly/yearly plans. This hustle picks up during the financial year-end but can give you steady income with regular clients. Which one are you planning to get started with? 💬

𝗜 𝗯𝘂𝗶𝗹𝘁 𝗮 𝗺𝗶𝗹𝗹𝗶𝗼𝗻-𝗱𝗼𝗹𝗹𝗮𝗿 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝗯𝗲𝗳𝗼𝗿𝗲 𝗜 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗼𝗼𝗱 𝘁𝗵𝗲 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝗰𝗲 𝗯𝗲𝘁𝘄𝗲𝗲𝗻 𝗽𝗿𝗼𝗳𝗶𝘁 𝗮𝗻𝗱 𝗿𝗲𝘃𝗲𝗻𝘂𝗲. I was running EngineerBabu, closing deals, managing teams, and talking to investors. all while fundamentally misunderstanding my own financial health. Let that sink in for a moment. 𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝘂𝗻𝗰𝗼𝗺𝗳𝗼𝗿𝘁𝗮𝗯𝗹𝗲 𝘁𝗿𝘂𝘁𝗵 𝗮𝗯𝗼𝘂𝘁 𝘄𝗼𝗺𝗲𝗻 𝗲𝗻𝘁𝗿𝗲𝗽𝗿𝗲𝗻𝗲𝘂𝗿𝘀:  • Most of us weren't raised to understand money.  • We weren't taught to negotiate salaries.  • We weren't encouraged to study finance. So we learn the hard way. By nearly failing. By making expensive mistakes. I'm done with that model. Here are the finance basics every woman entrepreneur needs to understand: 𝟭. 𝗥𝗲𝘃𝗲𝗻𝘂𝗲 = 𝗣𝗿𝗼𝗳𝗶𝘁 Revenue is the money coming in. Profit is what's left after you pay for everything. Track both. Obsessively. 𝟮. 𝗖𝗮𝘀𝗵 𝗙𝗹𝗼𝘄 𝗶𝘀 𝗞𝗶𝗻𝗴  You can be profitable on paper and still go bankrupt. How? If your money is tied up in unpaid invoices while your bills are due. Cash flow = the actual money moving in and out of your business. 𝟯. 𝗨𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱 𝗬𝗼𝘂𝗿 𝗨𝗻𝗶𝘁 𝗘𝗰𝗼𝗻𝗼𝗺𝗶𝗰𝘀 How much does it cost you to acquire one customer vs the revenue generated. If acquisition cost > revenue per customer, you're in trouble, no matter how fast you're growing. 𝟰. 𝗞𝗻𝗼𝘄 𝗬𝗼𝘂𝗿 𝗕𝘂𝗿𝗻 𝗥𝗮𝘁𝗲 𝗮𝗻𝗱 𝗥𝘂𝗻𝘄𝗮𝘆 Burn rate = how much money you're losing per month. Runway = how many months until you run out of money. If you have ₹20 lakhs in the bank and you're burning ₹2 lakhs/month, your runway is 10 months. 𝟱. 𝗚𝗿𝗼𝘀𝘀 𝗠𝗮𝗿𝗴𝗶𝗻 𝘃𝘀. 𝗡𝗲𝘁 𝗠𝗮𝗿𝗴𝗶𝗻  Gross margin = revenue minus direct costs (like salaries for delivery team). Net margin = revenue minus ALL costs (including rent, software, marketing, etc). Gross margin tells you if your core business model works. Net margin tells you if your entire operation is sustainable. 𝟲. 𝗘𝗺𝗲𝗿𝗴𝗲𝗻𝗰𝘆 𝗙𝘂𝗻𝗱 𝗶𝘀 𝗡𝗼𝗻-𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝗯𝗹𝗲 Always have 6-12 months of operating expenses saved. 𝟳. 𝗦𝗲𝗽𝗮𝗿𝗮𝘁𝗲 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹 𝗮𝗻𝗱 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗙𝗶𝗻𝗮𝗻𝗰𝗲𝘀 𝗜𝗠𝗠𝗘𝗗𝗜𝗔𝗧𝗘𝗟𝗬 𝟴. 𝗟𝗲𝗮𝗿𝗻 𝘁𝗼 𝗥𝗲𝗮𝗱 𝗬𝗼𝘂𝗿 𝗙𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹 𝗦𝘁𝗮𝘁𝗲𝗺𝗲𝗻𝘁𝘀 You don't need to be an accountant. But you need to understand:  • P&L (Profit & Loss): Are you making or losing money?  • Balance Sheet: What do you own vs. what do you owe?  • Cash Flow Statement: Where is money actually moving? Stop outsourcing all financial understanding to your accountant or co-founder. Your company's financial health is YOUR responsibility. Not theirs. Yours. Learn. Ask. Study. Master this. #WomenEntrepreneurs #FinancialLiteracy #FounderJourney #WomenInBusiness #Entrepreneurship #Supersourcing #BusinessFinance

TikTok Shop is not messing around. At Spree, we're building a shoppable video platform, but also a studio where we help brands and creators onboard, market, and sell through social platforms. Think of it like influencer marketing in a post-cookie world: full funnel from awareness to purchase, but all in one short-form video. Recently, our TikTok Shop partnership has been getting a lot of love. A few interesting learnings from this holiday season: 1. 'Viral' products are a shortcut. We uploaded one 'viral product' into the system and started getting sales before we posted our first video. Naturally, we ordered a few hundred more ASAP. 2. TikTok Shop success aligns closely with the rules of great influencer marketing. Get a creator with an engaged, lean-in audience. Find a product they actually like that their audience will actually like. Sell by telling a story, not by telling viewers to buy. 3. Most brands want to be on TikTok Shop but don't know how. It's complex. But once you've done it dozens of times (per day, in our case) it moves fast. I don't care if you're a mom and pop stationary shop, a creator merch brand, or a Fortune 500: you want to experiment here with a team who knows this market. 4. Live is great, but don't sleep on shoppable VOD. A perfect 30 second video of a product can do the work of a one hour live stream. Both are valuable, but too many people are talking about live shoppable and not enough are talking about shoppable shortform. 5. Trends + Product = Sales. Wednesday Addams' dance is popping? Sell the costume. King Bach flashlight dance is trending? Sell the flashlight. Spotify Wrapped is everywhere? Sell headphones. 6. Creators beware: not all audiences want this. If you make gold digger prank content, don't start selling The Feminine Mystique hardcover. If you are a creator and want to try it, make great content first and let a brand ride along. 7. Create like a creator. This is the rule for every brand on every social platform, but certainly pertains here. Don't do one tentpole shoppable live stream on TikTok and judge TT Shop on that. You need to habituate your audience, build a format, and keep it entertaining. In case you can't tell, this is addicting for a social media wonk like me. Smart influencer marketers are already testing this market understanding it will be a huge part of their ecommerce future. And those who haven't need to start today. #ecommerce #creatoreconomy #tiktok https://lnkd.in/e926z8zm

Founders, prove the sale before you hire the seller... The first sales hire should walk into a working system, not a blank page. Here is the minimum starter kit I believe every founder needs in place: 1️⃣ Define your ICP in detail. Company size, vertical, persona, pain. If anyone on your team cannot name it instantly, you are not ready. 2️⃣ Map pain to clear outcomes. List the top three problems that make prospects lose sleep and the measurable wins your product gives them. 3️⃣ Choose your entry path. Bottom up, top down, or both. Run small tests and note which path shortens time to value. 4️⃣ Set up a lightweight CRM early. A single source of truth for stages, notes, and next steps keeps momentum high when leads hit double digits. 5️⃣ Stress‑test your messaging and deck. Show drafts to prospects until they finish your sentence for you. Keep only the slides that trigger the aha moment. 6️⃣ Charge real money, even for pilots. Paid trials beat free trials every time. Revenue is the only true product‑market fit signal. 7️⃣ Write down common objections and winning rebuttals. New reps should learn from your scar tissue, not repeat it. 8️⃣ Baseline the funnel. Track lead‑to‑demo, demo‑to‑close, and average deal size so the first sales hire knows what good looks like. 9️⃣ Create a two‑week onboarding plan. Goals, shadow calls, product deep dive, and first‑week KPIs. Hand it over on day one. 🔟 Block time to coach. Hiring a rep does not mean you stop selling. Plan weekly deal reviews so they ramp fast. Once you can tick these boxes, bringing in a salesperson is an accelerator, not a rescue mission...

A frustrated PM used TechCrunch Disrupt to start a $1.7B unicorn. This is the wild story… 11 years ago, Hubert Palan was just another product manager. Now companies like Salesforce, Zoom, and Autodesk use his product: ___ 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟭: 𝗙𝗿𝗼𝗺 𝗮 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 𝗠𝗮𝗻𝗮𝗴𝗲𝗿'𝘀 𝗣𝗮𝗶𝗻 In 2014, Hubert struggled updating roadmaps on airplane wifi. "I was spending more time managing spreadsheets than talking to customers and building products," he recalled. Engineers had JIRA, sales had CRM, but PMs were drowning in an endless stream of spreadsheets and presentations. This pain led him to partner with Daniel Hejl to create a dedicated system of record for product management. ___ 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟮: 𝗙𝗶𝗻𝗱𝗶𝗻𝗴 𝗣𝗿𝗼𝗱𝘂𝗰𝘁-𝗠𝗮𝗿𝗸𝗲𝘁 𝗙𝗶𝘁 After launching at TechCrunch Disrupt in 2016... They focused on helping PMs utilize customer feedback. They quickly evolved to solve three core problems: - Centralizing customer insights - Prioritizing features strategically - Communicating roadmaps effectively Their traction came from mid-sized tech companies, Whose PMs were drowning in scattered feedback. By 2018, they did $8M Series A from Kleiner Perkins. Extended with an additional $10M the following year. __ 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟯: 𝗘𝘃𝗼𝗹𝘃𝗶𝗻𝗴 𝘁𝗵𝗲 𝗚𝗧𝗠 𝗘𝗻𝗴𝗶𝗻𝗲 By 2019, they raised a $45M Series B led by Sequoia. Transforming from a "tool" into a collaborative platform. Next year when the pandemic hit, It further accelerated digital adoption across all industries. In 2021, they were valued at $1.7 billion. Their growth formula was consistent: - Start with a passionate individual PM - Expand to their team, then division - Then secure a global deployment ___ 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟰: 𝗣𝗿𝗲𝘀𝗲𝗻𝘁-𝗗𝗮𝘆 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 Today, Productboard serves over 5,500 customers including companies like: Salesforce, Zoom and VMWare. While tech companies were the initial target... They've also expanded significantly into other verticals. With the end goal of creating that internal mindset shift: "If it doesn't live in Productboard, it doesn't exist." ___ 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟱: 𝗧𝗵𝗲 𝗙𝘂𝘁𝘂𝗿𝗲 Now they're becoming a multi-product AI company. "AI has finally unlocked the vision I've had for the last 10 years," says Hubert. Their new offerings like Productboard Pulse analyze feedback, identify trends, and suggest priorities. Which enables expansion into strategic planning with OKRs, setting the stage for continued market dominance. ___ If you want to dive deep into how they build product, their 7 layer of GTM strategy, and more... Go here: https://lnkd.in/eAJ2N_vW I've interviewed 7 Productboard leaders, talked to 3 customers, and read everything available about the company.