How to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund

Aug 7, 2022 Episode Page ↗
Overview

Ryan Hoover, founder of Product Hunt and investor at The Weekend Fund, shares insights on startup challenges, fundraising, launching products, and investment strategies. He discusses the importance of founder mindset, idea generation, and balancing public persona with personal vulnerability.

At a Glance
28 Insights
1h 9m Duration
18 Topics
6 Concepts

Deep Dive Analysis

Founder Anxiety and Vulnerability

Ryan Hoover's Public Persona and Personal Life

Leveraging Twitter DMs for Founder Advice

When to Start a Company and Fundraising

Revisiting Product Hunt's Fundraising Strategy

Strategic Reasons for Product Launches

Keys to a Successful Product Hunt Launch

Product Management Skills in Venture Capital

Product Hunt's Evolution and Monetization Lessons

Delegation Challenges for Founders

Life and Business: Momentum and Relationships

What Would You Rather Upvote? Game

Challenges of Building Consumer Startups

Strategies for Generating Startup Ideas

Importance of Niche Focus for Startups

Surprising Lessons from Angel Investing

Pathways and Advice for Aspiring Investors

The Future of The Weekend Fund and Building

Founder's Mask

Founders and CEOs often feel compelled to project an image of confidence and control externally, even when experiencing significant internal anxiety, stress, and worry. This 'mask' is worn to maintain trust and avoid burdening their team with their own anxieties.

Experimental Mindset

Approaching a new idea or project as an 'experiment' rather than a definitive 'startup' shifts the goal from immediate success to learning and adaptation. This mindset encourages tinkering and building to see if people want the product, making it a valuable way to start.

Momentum in Startups

Momentum is a crucial, reflexive force in early-stage startups. High momentum generates more high momentum, and low momentum leads to more low momentum, creating an energy that influences team motivation, shipping speed, and overall company trajectory.

Problem Journal

A method for generating startup ideas by simply writing down observations of things that are annoying, inefficient, or problematic, without immediately trying to devise solutions. This helps identify unmet needs and potential opportunities.

Good Hygiene in Investing

Refers to the operational best practices in running a fund, such as consistently responding to founders (even with a pass), providing context for rejections, and following up with introducers. This builds goodwill and maintains professional relationships within the ecosystem.

Pretend Angel Investing

A strategy for aspiring investors to gain experience and prove their abilities without needing capital. It involves creating a fantasy portfolio, writing investment memos for companies they would have backed, and outlining their thought process behind those decisions.

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What is the biggest challenge founders face regarding transparency?

Founders often struggle with the 'mask' of confidence, feeling they must project strength externally while dealing with internal anxiety, making it hard to be fully transparent with their team without causing undue worry.

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When should someone decide to start a company?

It's advisable to only start a company if you feel an undeniable drive to do so, and you can envision yourself working on the idea for at least a decade, using an experimental mindset to test and learn rather than immediately aiming for a full-fledged startup.

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Why should a company launch a product?

Launches serve multiple purposes beyond just customer acquisition, including recruiting talent, generating fundraising momentum, gathering user feedback, fostering partnerships, boosting team morale, and improving SEO.

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What makes a product launch successful, especially on platforms like Product Hunt?

Successful launches often use authentic, human language in their messaging rather than PR-speak, keep descriptions brief, and utilize visuals (like a gallery slideshow) to tell a compelling story and capture interest.

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What skills from product management are most valuable for early-stage startup investing?

A product management background is highly valuable because it provides perspective for evaluating ideas, understanding market needs, and, crucially, assessing a founder's thought process and ability to develop product insights.

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What are common mistakes founders make when building a company?

Common mistakes include expanding horizontally into too many different product categories instead of focusing vertically, delaying monetization efforts, and struggling with delegation due to a desire for control and perfectionism.

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What matters most in life and business?

In life, authentic, deep relationships with a few close friends become increasingly important over time. In business, momentum is paramount, as it's reflexive and drives energy, motivation, and overall company trajectory.

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Why are consumer startups so difficult to succeed with?

Consumer startups face challenges like harder monetization (often requiring massive scale for advertising), intense competition for user attention (even from unrelated services like Netflix), and the difficulty of overcoming established user habits and internal triggers for existing products.

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How can one come up with good startup ideas?

Useful methods include keeping a 'problem journal' to note daily annoyances, immersing oneself in niche communities to observe unique insights and patterns, and closely watching consumer behavior shifts (e.g., remote work) and technology shifts (e.g., mobile, AI, Web3).

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Why is it important for startups to focus on a narrow target audience initially?

A narrow focus makes it easier to build a great solution, hone the product experience, and craft precise marketing messages for that specific group. While it might seem limiting, it often leads to opportunities for broader expansion later.

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What is a surprising lesson learned from angel investing?

A surprising lesson is that companies you might have written off can still succeed through pivots, unexpected partnerships, or M&A events, highlighting the resilience of founders and the importance of not counting a portfolio company out until it's truly over.

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What are different ways to get into investing or angel investing?

Options include direct angel investing (if you have capital and are willing to lose it), joining scout funds (dedicated programs or deal-sharing for carry), using Special Purpose Vehicles (SPVs) for single-company investments, or raising your own fund.

1. Start Only If You Must

Only start a company if you feel an irresistible urge to do so, as the journey is exceptionally challenging and often leads to failure.

2. Adopt an Experimental Mindset

Approach new ideas by tinkering and building them as experiments, prioritizing learning and validating demand over immediate success.

3. Commit for a Decade

Before committing to a startup, use a ‘decade rule’ litmus test: ask yourself if you genuinely care enough about the idea to work on it for at least ten years.

4. Balance Founder Authenticity

As a founder/CEO, strategically balance your desire for authenticity with the need to maintain an outward appearance of confidence, as full transparency about anxieties can undermine trust and morale.

5. Delegate Early & Trust

Actively practice delegation and trust your team members, even if it means accepting minor mistakes, as it’s essential for scaling yourself and the company, ultimately leading to a net positive outcome.

6. Prioritize 100% Ownership

Aim to own 100% of your creation for as long as possible, as raising venture capital is a ‘one-way door’ that can always be opened later if strategically necessary.

7. Cultivate Startup Momentum

Actively cultivate and maintain momentum in early-stage startups, as it’s a reflexive force where positive energy from shipping and progress encourages further high performance.

8. Keep a Problem Journal

Note down observations of inefficiencies or annoyances in daily life in a ‘problem journal,’ focusing purely on articulating the problem without immediately trying to devise a solution.

9. Immerse in Niche Communities

Immerse yourself in diverse, especially niche or long-tail, communities (e.g., subreddits, hobbyist groups) to observe patterns, identify shared problems, and uncover unique insights for startup ideas.

Generate startup ideas by observing significant consumer behavior shifts (e.g., remote work) and technological advancements (e.g., mobile, AI, Web3), asking ‘why now?’ to identify what new solutions are uniquely possible today.

11. Focus Vertically, Not Horizontally

For platform growth, focus vertically on serving your core community deeply rather than attempting broad horizontal expansion into disparate communities, which is often harder than anticipated.

12. Monetize Early & Consistently

Dedicate a small but consistent portion (e.g., 10%) of your focus to revenue generation early on, even when prioritizing growth, as achieving cashflow break-even provides significant flexibility and control over your destiny.

13. Define Launch Goals Clearly

Before launching, clearly define your primary goal beyond just customer acquisition; consider other strategic benefits like recruiting, fundraising, gathering feedback, fostering partnerships, boosting team morale, or improving SEO.

14. Leverage Launches for Morale

Use product launches as a powerful team morale-building moment, allowing the team to celebrate accomplishments and share their work with the world.

15. Write Like a Human

When crafting launch messaging, avoid ‘PR speak’ and instead write like a human, using language your customers or friends would use to describe your product, as this resonates more authentically.

16. Optimize Product Hunt Launch

For a successful Product Hunt launch, use human, brief language in your tagline and maker introduction, and leverage the visual gallery as a storytelling slideshow to capture user interest.

17. Narrow Your Target Audience

Focus on a very narrow target audience initially, as this simplifies building a tailored product and marketing message, and don’t fear it being too niche as expansion opportunities often emerge later.

18. PM Skills for Founders/Investors

Recognize that product management skills are highly valuable for both early-stage founders and investors, providing critical perspective for evaluating ideas and assessing a founder’s thought process.

19. Practice Investing Hygiene

In investing, always provide clear, constructive feedback to founders, even when passing, and consistently follow up with introducers to maintain strong relationships.

20. Never Count Out a Company

As an investor, never prematurely write off a portfolio company, as resilient founders can pivot or encounter unexpected opportunities (e.g., partnerships, M&A) that lead to success.

21. Explore Investing Paths

Consider various ways to get into investing: angel investing (if capital allows), scout programs, Special Purpose Vehicles (SPVs) for single deals, or raising your own fund.

22. Create a Fantasy Portfolio

If direct investing isn’t an option, create a ‘fantasy portfolio’ by writing investment memos for companies you’re excited about, demonstrating your thought process and abilities to potential employers or partners.

23. Prioritize Deep Relationships

Cultivate a few deep, authentic relationships over a large quantity of acquaintances, as these connections become increasingly valuable with age.

24. Evaluate Cities as Products

When considering where to live, evaluate cities like products, weighing their ‘costs’ (cost of living, taxes) against their ‘benefits’ (lifestyle, friends, amenities) to find the best ROI for your personal needs.

25. Introverts: Manage Social Energy

Introverts attending social events should be aware of their energy limits and plan for breaks or exits to manage social exhaustion.

26. Consider Public Perception

Before publicly announcing personal moves or changes, consider the public perception and potential lack of benefit, especially if it aligns with a trending narrative.

27. Open DMs for Content

To generate content and refine your thinking, consider opening your DMs for specific questions from your audience and using their prompts as a basis for ‘micro-blog posts’ (e.g., on Twitter), ensuring anonymity for sensitive information.

28. Adopt a Curator Approach

When creating content or offering advice, consider a ‘curator’ approach by pulling in domain experts to answer questions, which can lead to better, more useful content and potentially be easier than trying to answer everything yourself.

You have to put on this space of confidence externally and internally as well, where people need to trust you. You also don't want to subject them to the same anxiety that you're feeling and be 100% transparent.

Ryan Hoover

My general advice to founders is like, don't start a company unless you just like, can't not start a company because it's so hard.

Lenny Rachitsky

I think it's super important that founders see a line of sight to work on this for, I think my rule of thumb is a decade.

Ryan Hoover

I think a lot of people also think I need to start a company. I need to start a startup. And they skip to that step without just tinkering and building.

Ryan Hoover

I think the language and the micro copy copywriting matters so much. And the people that use buzzwords and, and vague language, it just doesn't click.

Ryan Hoover

Never count a portfolio company out until it's over.

Ryan Hoover

Cliches and platitudes are cliches and platitudes because we've heard them so many times, but that because they're true, people just say them because they're so true.

Lenny Rachitsky

Problem Journal for Startup Ideas

Ryan Hoover
  1. Observe things that annoy you or are inefficient in your daily life or within communities.
  2. Write them down as specific problems or unmet needs.
  3. Do not immediately try to come up with solutions; focus only on documenting the problem.

Pathways to Getting into Investing

Ryan Hoover
  1. Angel Investing: Use personal capital if available and be willing to lose it, understanding it's a long-term play.
  2. Scout Funds: Join scout programs to deploy capital or earn carry on deals, often with less autonomy than running your own fund.
  3. Special Purpose Vehicles (SPVs): Raise money from Limited Partners (LPs) for single-company investments, offering deal-by-deal carry but requiring significant fundraising effort per deal.
  4. Raising a Fund: Commit to the extensive work of raising capital and managing a fund, which offers maximum flexibility and the ability to deploy many checks.
  5. Pretend Angel Investing: Create a fantasy portfolio and write investment memos for companies you would have backed to prove your abilities and thought process without actual capital.
late 2013
Product Hunt founding When Product Hunt started
4-5 months
Product Hunt incorporation Time after starting until Product Hunt was incorporated
a decade
Ryan Hoover's rule of thumb for founder commitment Time founders should envision working on a company
after acquisition
Product Hunt revenue generation When Product Hunt started trying to make money (after being acquired by AngelList)
12 months
Product Hunt cashflow break-even Time after starting to generate revenue until cashflow break-even
10 hours
Typical essay writing time for Lenny's newsletter (median) For a typical post on Lenny's newsletter
hundreds of hours
Typical essay writing time for Lenny's newsletter (epic posts) For the most epic posts on Lenny's newsletter
two-thirds of the year in Miami, one-third elsewhere
Ryan Hoover's current location split For Ryan and his girlfriend
over 110 companies
Number of companies Weekend Fund has invested in Total investments to date
21 million
Weekend Fund's latest fund size Size of their third fund
30-35% deployed
Weekend Fund's deployment status Of their third fund