🪴 The ultimate founder playbook
Always know what you next step is ✨
Throughout our lives we’ve all experienced the constant guidance of others — be it parents, friends, teachers, or bosses. Guidance shaping our paths and decisions.
It’s become awfully quiet now.
Becoming a founder means stepping into unknown, on a daily basis. The familiar voices guiding us are starting to fade. Now, it’s all on us.
Every decision counts. Every task matters. We create our own schedule, strategise our next move.
If we don’t, no one else will. It’s a relentless cycle of effort, uncertainty, and persistence.
So I decided to create a guide to navigating the complex landscape of entrepreneurship. It’s filled with actionable insights and proven strategies to help us find the path forward.
🧠 Idea Generation
Create a problem mindset; start noticing things that do not work well and think of potential improvements (e.g. Uber, Stripe).
Solve personal pain points; if it bothers you, chances are it bothers others (e.g. Slack, Dropbox).
No idea is a bad idea (e.g. Disney).
Interview potential users to find out the biggest problems they face (e.g. Airbnb).
Do hackathons to test out random ideas under time pressure (e.g. Instacart).
Review trending patents or academic papers to discover emerging technologies that can inspire new solutions (e.g. OpenAI).
Reverse engineer successful products to understand why they work and how you can apply similar principles in other areas (e.g. Facebook).
Look for cross-industry trends — something working in one field might be missing in another (e.g. Discord).
Challenge your assumptions by asking "what if?" and breaking conventional thinking patterns (e.g. SpaceX).
Ask ‘How might we...’ questions that open up creative problem-solving, such as "How might we make remote work more enjoyable?" (e.g. WeWork).
Collaborate with others from different fields for fresh perspectives (e.g. Apple).
Focus on simple solutions first; what small, impactful feature can fix a widespread problem? (e.g. Twitter).
📈 Business Model
Clearly define the problem you’re solving and the value you provide (e.g. Canva).
Study your competitors to understand the exploitable gaps in the market (e.g. Zoom).
Test different revenue streams; freemium, subscription, or transaction-based and see what resonates with your customers (e.g. Spotify).
Focus on recurring revenue for long-term stability (e.g. Salesforce).
Network effects; the more people use your product, the more valuable it becomes for others (e.g. Facebook, LinkedIn).
Use waitlists and pre-selling to validate your business model quickly (e.g. Superhuman, Robinhood).
Know your metrics, such as customer acquisition cost, lifetime value.
Don’t be scared to pivot if things don’t work out (e.g. Tiny Speck → Slack, Odeo → Twitter).
Look for possible partnerships (e.g. Uber and Spotify integration).
Offer different pricing plans and tiers to attract a variety of customer segments (e.g. Beehiiv).
Experiment with a loss leader — offer something for free or low-cost to draw in customers, then upsell later (e.g. Kindle, Netflix with ads).
Analyze customer behavior data to find opportunities for cross-selling or upselling (e.g. Netflix recommendation).
Integrate affiliate programs where partners get paid to promote your product (e.g. Amazon, Beehiiv).
Simplify your pricing model (e.g. Chilipiper, Basecamp).
Focus on sustainable growth by balancing short-term profits with long-term customer relationships (e.g. Patagonia).
Identify strategic resources needed to succeed, whether it’s technology, partnerships, or talent (e.g. Tesla focusing on battery production).
Create an ecosystem; build complementary products or services that feed into each other (e.g. Apple).
Leverage user-generated content to lower costs and increase engagement (e.g. Trustpilot, Airbnb).
📦 Minimum Viable Product
Only solve one essential problem first (e.g. Dropbox).
Create a simple prototype to test the concept quickly before investing in full development (e.g. Figma’s early wireframe mockups).
Get user feedback early and often to ensure you’re building what the market needs (e.g. Airbnb pivoted based on host feedback).
Launch with a small, focused feature set; avoid feature creep and stick to essentials (e.g. Instagram).
Niche down and test your MVP on a small scale (e.g. Facebook started on Harvard’s campus only).
Use landing pages to gauge interest before even building the product (e.g. Buffer).
Measure key metrics early; track user engagement, retention, and feedback from day one to validate your hypotheses.
Iterate rapidly based on feedback; again — don’t be afraid to pivot (e.g. Slack pivoting from a failed gaming startup).
Perfectionism is procrastination masquerading as quality control; launch as quickly as possible (e.g. Twitter, Facebook,
Apple).Stay lean; build only what’s necessary and cut anything that doesn’t contribute to solving the core problem (e.g. Airbnb’s early MVP was simply renting air mattresses).
Offer early access to a small group to gather focused feedback and build excitement (e.g. Clubhouse, Breezi).
Set clear validation goals; decide upfront what success looks like (e.g. number of signups, usage rates) and measure against those.
Offer a simple onboarding experience to get users hooked on your MVP quickly (e.g. Slack’s seamless team setup).
Make your MVP look professional even if it’s simple — presentation still matters to early adopters (e.g. Stripe — I can’t emphasise enough how good that landing page is).
🤝 Team Building & Culture
Hire for passion; focus on people who are genuinely excited about your mission and can grow with the company (e.g. early Airbnb).
Define your company values early on, and make sure every new hire embodies them (e.g. Netflix, Amazon).
Foster a transparent culture by openly sharing company goals, progress, and challenges (e.g. Buffer).
Gamify your onboarding (e.g. Twilio).
Learn and build in public.
Create an environment where everyone feels empowered to contribute ideas, regardless of their role (e.g. Google’s 20% time for personal projects).
Avoid politics for as long as possible (e.g. Spotify).
Lead by example; founders should model the behaviours they want to see in the team (e.g. Elon Musk’s hands-on leadership at Tesla).
Celebrate small wins to boost morale and keep the team motivated (e.g. Trello).
Encourage open feedback loops between team members and leadership to foster continuous improvement (e.g. Bridgewater).
Foster a strong onboarding experience so new hires feel supported from day one (e.g. Zappos).
Incorporate regular team-building activities and off-sites to strengthen bonds and improve collaboration (e.g. GitLab).
Remote work doesn’t always work. Hybrid model strikes a good balance, I guess? (e.g. Barclays).
Build a flat hierarchy for open communication between all levels of the company (e.g. Valve).
Ensure psychological safety; create an environment where team members feel comfortable sharing ideas and taking risks without fear of failure (e.g. Google).
Instill a sense of ownership by offering equity or profit-sharing (e.g. Facebook’s early employee stock options).
💰 Fundraising & Investor Relations
Build a strong pitch deck that clearly communicates your vision, problem, solution, and market potential (e.g., Passionfroot).
Develop relationships with investors early, long before you need to raise money.
Validate your market early to show traction and product-market fit (e.g., Slack).
Leverage your network to warm up introductions to potential investors (e.g., WhatsApp, Stripe).
Seek investors who align with your sector or mission (e.g., Elon Musk securing mission-driven investors for Tesla and SpaceX).
Know your unit economics and growth strategy inside out.
Demonstrate a clear path to revenue and profitability, even if you're not profitable yet (e.g., Facebook focused on growth first, then monetized later).
Run fundraising as a sprint; focus intensely on it for a short period to minimize distractions.
Do regular investor updates (e.g., Beehiiv).
Create a sense of urgency by setting a deadline for your fundraising round to close.
FOMO works: Make investors feel that "It happens with or without you."
Balance valuation with ownership; avoid over-raising too early and losing control.
Prepare for term sheet negotiations; know what's non-negotiable.
Leverage accelerators or incubators for early traction and credibility.
Launch on ProductHunt. It’s a must.
Master storytelling. Frame your startup journey as a compelling narrative (e.g., Steve Jobs’ storytelling for Apple).
Get feedback from investors who pass to improve your pitch and address concerns.
Prepare a data room with financial projections, cap table, and legal docs.
Showcase your team’s strength. Investors bet on teams, so highlight your founding team's experience and track record.
📢 Customer Acquisition
Identify your target audience early by creating detailed buyer personas (e.g., HubSpot).
But don’t get lost in hypotheses. Execution matters.
Leverage content marketing to attract potential customers (e.g., Buffer).
Run small-scale ad campaigns to test channels and optimize acquisition.
Focus on organic growth; build a community and engage through social media.
Offer referral programs (e.g., Dropbox’s famous referral system).
Invest in SEO early.
Build a pre-launch waiting list to create buzz (e.g., Robinhood’s invite-only launch).
Virality is your best friend. Design shareable experiences.
Use scarcity and urgency to drive conversions.
A/B test everything—landing pages, emails, pricing.
Engage in community forums (e.g., Quora, Reddit, Product Hunt).
Leverage PR to get featured in key publications.
Balance incentives between acquiring new customers and retaining existing ones (e.g., definitely not Beehiiv).
💵 Sales & Revenue Growth
Have a clear sales process to guide customers from lead to conversion.
Set specific, measurable sales targets.
Use CRM software to track leads, sales, and customer interactions.
Train your sales team on product knowledge, objection handling, and closing techniques.
Research your leads before reaching out.
Leverage content marketing for sales funnels.
Webinars? Maybe. But optimize your time—few people join them.
Network within your industry at events and conferences.
Create a referral program for exponential growth.
Nurture leads with email campaigns until they're ready to buy.
Segment your customer base to tailor sales strategies.
Offer flexible payment options or financing.
Build an affiliate program to drive additional revenue.
Hire Reddit & Quora ambassadors to pitch your brand.
Optimize your sales funnel to reduce friction and boost conversions.
Implement a loyalty program to retain customers.
Adjust pricing strategies based on demand, competition, and perceived value.
🌈 Scaling to Infinity
Systematize operations so growth doesn’t break your business.
Automate processes to reduce manual work (e.g., Zapier, Notion workflows).
Build a hiring pipeline to scale your team efficiently.
Establish a strong company culture to retain top talent.
Diversify acquisition channels to avoid over-reliance on one.
Expand into new markets when the time is right.
Develop partnerships to accelerate growth.
Measure key metrics obsessively and iterate fast.
Stay cash-efficient. Scale too fast, and you’ll burn out.
Think global from day one.
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Sincerely,
Oliver 👋