Jason Fried challenges your thinking on fundraising, goals, growth, and more

Jason Fried challenges your thinking on fundraising, goals, growth, and more

The Benefits of Bootstrapping for Entrepreneurs

The Value of Making Money

  • Bootstrapping allows entrepreneurs to practice the fundamental skill of making money, which is essential for running a successful business.
  • The common narrative in the industry promotes "go big or go home," often leading to raising significant funds and aiming for unicorn status, but this approach is not as effective as it seems.

Alternative Paths to Success

  • Jason Fried, Co-Founder and CEO of 37signals (now Basecamp), exemplifies a different business model: no investors, no board, and consistent profitability over 24 years.
  • Many founders default to venture capital routes; however, bootstrapping can be more fulfilling and lucrative by fostering creativity within constraints.

Insights from Jason Fried on Business Strategy

Decision-Making and Planning

  • Constraints like small teams often lead to better outcomes in decision-making processes.
  • Gut instinct is an underappreciated tool in making decisions; relying solely on long-term planning can be a mistake.

Work Culture and Mindset

  • Work does not have to feel like a battle; focusing on playing infinite games rather than finite ones can change perspectives on success.
  • Understanding when to consider raising venture capital versus bootstrapping is crucial for entrepreneurs.

Sponsorship Messages

Coda's Role in Team Efficiency

  • Coda helps streamline team operations by centralizing data across various formats, enhancing collaboration.

Sidebar's Personal Board Concept

  • Sidebar offers senior leaders access to peer groups that provide unbiased opinions and diverse perspectives for career growth.

Contrarian Perspectives with Jason Fried

Understanding 37signals' Success

  • Lenny introduces a new segment called Contrarian Corner, emphasizing the unique success story of 37signals.

Business Profitability and Growth Strategies

Overview of Business Performance

  • The speaker highlights a consistent profitability over 24 years, with double-digit million dollar profits annually for the last decade.
  • Emphasizes maintaining a small team (around 75 employees) while serving over 100,000 paying customers, focusing on simplicity rather than complex metrics.

Philosophy on Revenue and Experimentation

  • The goal is to earn more than spent, ensuring healthy margins that allow for experimentation without fear of failure.
  • Critiques the venture capital approach where companies prioritize rapid growth at the expense of immediate profitability.

When to Raise Capital

  • Advises founders to consider raising funds only when necessary for tangible assets or operational costs, such as in manufacturing or restaurant businesses.
  • Points out that software businesses typically require minimal initial investment (e.g., laptops), making them less reliant on external funding.

Silicon Valley Economics vs. Traditional Business Models

  • Discusses how Silicon Valley has turned potentially high-margin software businesses into low-profit entities due to excessive spending on customer acquisition and staffing.
  • Contrasts traditional business challenges (like physical goods and competition pricing) with the advantages of software economics.

The Case Against Venture Capital

  • Argues that venture-backed companies often miss opportunities by focusing solely on becoming massive instead of finding sustainable niches.
  • Highlights the risks associated with venture backing, suggesting it can lead to unsustainable growth pressures that may harm smaller businesses.

Efficiency Over Growth: A Different Approach

Comparison with Competitors

  • Compares employee counts among competitors like Asana and Slack versus their own lean operation with around 75 employees while achieving similar customer numbers.

Focused Business Model

  • Attributes success to an efficient business model focused on profitability rather than expansion; avoids unnecessary complexity in offerings or sales strategies.

Simplified Pricing Strategy

  • Maintains a straightforward pricing structure without multiple tiers or extensive customization options, which reduces overhead costs significantly.

Understanding the Value of Small Teams

The Benefits of Simplicity and Focus

  • Emphasizes building a single, well-crafted product to avoid complexity associated with catering to diverse companies with varying needs and expectations.
  • Highlights a unique development approach where only two people (one programmer and one designer) work on features for a maximum of six weeks, promoting efficiency and quick decision-making.
  • Warns against the pitfalls of hiring excessively, noting that financial capability does not justify unnecessary expansion which can lead to operational chaos.

Constraints as Catalysts for Success

  • Argues that constraints foster simplicity and honesty in operations, allowing the company to focus on serving small businesses effectively rather than pursuing larger corporations with complex sales processes.
  • Expresses skepticism about large organizations' ability to function efficiently due to their inherent complexity and multiple layers of management.

Perspectives on Size and Effectiveness

  • Discusses the idea that remaining small is not merely a transitional phase but can be an ideal state for effectiveness.
  • Quotes: "Small is not just a stepping stone; small is a great destination itself," emphasizing the value found in maintaining smaller teams.

Defining Success Beyond Growth Metrics

  • Shares insights on success being defined by personal enjoyment in work rather than traditional metrics like revenue or customer growth.
  • Contrasts two paths: scaling massively versus focusing on profitability without needing widespread adoption.

Profitability vs. Data-driven Decisions

  • States that success hinges on whether one would want to repeat their experiences, suggesting subjective measures over objective data analysis.
  • Clarifies that while profitability is essential, it’s viewed collectively rather than through detailed profit-and-loss statements for each product.

Values Over Financial Goals

  • Advocates for making decisions based on what feels right rather than strict financial goals or performance indicators.

The Philosophy of Infinite Games

The Concept of Infinite vs. Finite Games

  • The book discussed emphasizes the importance of engaging in infinite games for happiness, contrasting them with finite games that have specific end goals, such as selling a business or achieving a promotion.
  • The speaker reflects on their career journey, starting from age 13 and how they view their work as a continuous process rather than isolated achievements.

Continuity in Career Choices

  • The speaker draws parallels between past experiences selling electronics and current software sales, highlighting a consistent passion for building and selling useful products.
  • They express a desire to create an enduring company where they can continue working indefinitely, emphasizing entrepreneurship as a long-term commitment rather than just a job.

Independence in Business

  • The speaker values the independence of running an independent business without external pressures or obligations to sell or change direction based on investors' demands.
  • They reject the idea of short-term investment strategies that require abandoning enjoyable work for financial gain, preferring to focus on sustainable practices.

Celebrating Longevity Over Startups

  • A distinction is made between "startups" and "stay ups," with the latter being celebrated for their resilience and ability to endure beyond initial growth phases.
  • Starting a business is deemed easier than maintaining it; staying relevant over time presents greater challenges due to competition and market changes.

Challenges of Sustaining Growth

  • The speaker discusses common pitfalls faced by new businesses, including stagnation after initial success and the need for genuine interest in one's work to overcome plateaus.
  • They acknowledge that while starting something may be easy, sustaining momentum requires dedication and adaptability through fluctuating circumstances.

Reflections on Long-Term Commitment

  • As someone who has been in business for nearly 25 years, the speaker shares insights about periods of doubt regarding longevity but also expresses renewed excitement about their current endeavors.

Reflections on Leadership and Business Growth

The Challenge of Hard Work

  • The speaker reflects on the nature of hard work, contrasting past experiences with current challenges. They reminisce about simpler times when the company was smaller, acknowledging that while it was easier, circumstances have changed.

Milestones and Future Aspirations

  • Approaching a milestone birthday and 25 years of running the company prompts introspection. Despite contemplating whether it's time to step back, there is excitement about ongoing product development and future projects like ONCE.

Energy Dynamics in Business

  • The speaker discusses their fluctuating energy levels related to business operations. Currently feeling energized by their work, they acknowledge past periods where the business drained their enthusiasm.

Curiosity About Alternative Leadership

  • A recurring thought for the speaker is what another leader might do if they took over the company. This curiosity stems from a desire to understand different approaches to leadership without actually wanting to relinquish control.

Opportunities for Growth

  • The speaker believes that an outsider would likely focus on growth opportunities often overlooked by them. They express concern about being "stuck" in established routines rather than exploring new avenues for expansion.

Potential Changes Under New Leadership

  • Speculating on how someone else might run the company differently, the speaker suggests that new leadership could prioritize aggressive marketing strategies and product diversification, potentially sacrificing margins for growth.

Missed Opportunities and Market Expansion

  • Reflecting on missed opportunities within their brand, the speaker acknowledges potential markets (e.g., religious institutions or educational sectors). While these ideas don't personally excite them, they recognize their value in expanding business reach.

Alternative Paths in Business Strategy

Understanding Business Models: The Bootstrap Approach

The Reality of Most Businesses

  • Many businesses operate on a bootstrap model, lacking external funding and relying on personal investment to start.
  • Contrary to the perception of being outliers, most business owners manage their operations similarly, focusing on profitability and cost management.
  • While moonshot ventures are admirable, they are not the only path; this discussion emphasizes alternative approaches to business success.

Optionality in Business Success

  • The speaker advocates for exploring multiple avenues for success rather than adhering strictly to high-risk models like venture capital.
  • Acknowledges that while luck plays a role in business success, there are more opportunities available outside of the "go big or go home" mentality.

Venture Scale vs. Sustainable Ideas

  • Questions what defines a venture-scale company and highlights that many great ideas can thrive without massive funding.
  • Uses Basecamp as an example to illustrate how different approaches can lead to varying levels of success without needing to conform to venture-backed expectations.

Comparing Business Models

  • Discusses the potential for Basecamp's model to be adapted into a larger scale but expresses satisfaction with its current profitable state.
  • Emphasizes that mindset is crucial; companies can choose different paths based on their goals and values.

Examples of Venture-backed Necessities

  • Cites Airbnb and Uber as examples where rapid expansion is essential due to their physical product nature requiring widespread availability.
  • Highlights that these companies need significant initial investments for marketing and infrastructure compared to software-based businesses like Basecamp.

Innovative Development Methodologies at 37signals

Introduction to Shape Up Framework

Understanding the Concept of Appetites in Project Management

The Six-Week Appetite Framework

  • The approach emphasizes that any project should not exceed a six-week timeframe, framing this as an "appetite" rather than an estimate. This distinction highlights a commitment to time limits rather than vague predictions.
  • Each feature or task is assigned a maximum appetite of six weeks, which serves as the budget for development. Teams must focus on creating the simplest and most effective version within this constraint.
  • Not all tasks require the full six weeks; some may only need one week. The key is to recognize that work can expand to fill available time, so setting appetites helps maintain focus and efficiency.

Principles of Shaping Work

  • Fundamental principles include limiting projects to six weeks with small teams (maximum two people), allowing flexibility in how work is executed without rigid specifications or task lists.
  • Teams are empowered to determine how best to achieve their goals based on initial ideas and designs, fostering creativity and ownership over their work processes.

Managing Expectations and Trade-offs

  • During project execution, discussions about potential changes or challenges are encouraged. This process involves "trading concessions," where teams negotiate adjustments based on new insights gained during development.
  • If a project exceeds its six-week limit without significant progress, it typically gets canceled. Maintaining strict adherence to timelines prevents prolonged projects that can lead to demoralization among team members.

Visualizing Progress with Hill Charts

  • Basecamp utilizes "hill charts" to visualize project progress. Projects are likened to hills: early stages involve pushing uphill (problem-solving), while later stages represent downhill execution (implementation).
  • If a project nears completion but requires additional time (e.g., two more days), extensions may be granted. However, if significant challenges remain at the deadline, the project likely will not continue.

Implications of Shorter Project Cycles

  • Shorter cycles help prevent burnout from long-running projects that can lead employees to dislike their work or even leave their jobs due to frustration with unending tasks.
  • Recognizing that not all projects will be exciting allows teams to manage expectations better; knowing there’s a clear endpoint helps maintain morale even for less engaging tasks.

The Dangers of Promises in Business

  • Long-term planning is viewed skeptically; making promises about delivery times often leads businesses into trouble when deadlines are missed due to unforeseen complications.
  • Acknowledging that effort correlates directly with expected impact reinforces the appetite concept—if effort increases disproportionately without clear benefits, it raises questions about the project's viability.

Understanding the Challenges of Promising Work

The Risks of Long-Term Promises

  • Making promises about work to be completed by the end of the year can lead to disappointment; it's easy to overcommit when deadlines are far away.
  • Many companies are adopting new methodologies like Shape Up, but changing established work habits is challenging due to deeply rooted practices.

Metaphor of Growth and Change

  • Changing a company's workflow is akin to uprooting a plant; it requires planting new ideas and methods rather than trying to modify existing ones.
  • It's advisable to experiment with new methods on low-stakes projects first, as initial failures can discourage future attempts if applied to critical tasks.

Learning Through Experimentation

  • Trying out new approaches in less critical areas allows teams to learn without the pressure of high stakes, fostering growth and adaptation.
  • If a new method fails during a crucial project, it may prevent future experimentation due to negative comparisons with traditional methods that were merely adequate.

The Concept of Cycles vs. Sprints

Rethinking Work Phases

  • The term "sprint" implies exhaustion; instead, cycles should be viewed as ongoing processes that allow for recovery and preparation for future work.
  • After intense work periods (cycles), a two-week cooldown is implemented where team members can focus on lighter tasks or wrap up loose ends.

Benefits of Cooldown Periods

  • A cooldown period helps prevent burnout by allowing employees time for reflection and minor adjustments after intensive work phases.
  • During cooldown weeks, team members engage in various activities that contribute positively without the pressure of strict deadlines.

Decision-Making Based on Intuition

Embracing Gut Instinct in Operations

  • The speaker emphasizes an intuition-driven approach over data-driven decision-making, suggesting that all decisions ultimately involve judgment calls.

Understanding Decision-Making in Business

The Role of Judgment and Experience

  • Decision-making in business often transcends pure rationality; it involves complex judgment calls influenced by a myriad of known and unknown factors.
  • Companies prioritize hiring executives based on their judgment and experience rather than just technical skills like reading spreadsheets, as these qualities are more difficult to quantify.
  • Data is only one aspect of decision-making; many other intangible elements contribute to the process, which may not be fully understood even by the decision-maker.

Embracing Intuition

  • Acknowledging that intuition plays a significant role in decision-making can enhance confidence in one's choices, despite the lack of clear reasoning behind them.
  • Founders or leaders should give credit to their gut feelings, as they encapsulate accumulated experiences and insights that are valuable for making decisions.

Fostering an Intuitive Culture

  • Leaders can encourage team members to trust their instincts by modeling this behavior themselves during discussions about decisions.
  • Engaging team members with questions about how they feel regarding decisions fosters an environment where emotional input is valued alongside logical reasoning.

The Importance of Feelings in Decision-Making

  • In workplace discussions, asking "how does this feel?" becomes crucial as it acknowledges that human beings primarily operate from a place of feeling rather than pure logic.
  • This approach encourages open dialogue about subjective experiences related to products or features being developed, enhancing collaborative decision-making.

Navigating Uncertainty

  • The focus should not be on certainty but rather on understanding how ideas resonate emotionally within the team.
  • The thought process leading up to decisions can be messy and non-linear; clarity often emerges through discussion and exploration over time.

Trusting Instinct vs. Experience

  • While instinct is powerful, not everyone possesses strong intuitive skills; hiring experienced individuals can help balance this gap within teams.

Hiring Designers: Understanding Their Instincts

The Importance of Designer Tastes

  • The speaker emphasizes the significance of understanding designers' tastes and influences during the hiring process, as it reveals their perspective and potential contributions to the company.

Project-Based Evaluation in Interviews

  • Finalists for design positions are required to complete a project, which is compensated. This allows the interviewer to assess their practical skills and creativity under time constraints.

Critique and Instinctual Responses

  • During critiques, even if the work is well-received, the speaker challenges candidates by asking how they would improve their project with more time. This tests their instinctual responses and creative thinking.

Assessing Raw Creativity

  • The speaker looks for candidates who can generate ideas on-the-fly, indicating a rich internal reservoir of creativity. Candidates should be able to riff spontaneously rather than relying solely on premeditated concepts.

Synchronicity in Collaboration

  • A key indicator of a good hire is the ability to engage in collaborative brainstorming that feels harmonious. When both parties resonate creatively, it signals a strong potential fit within the team.

Balancing Ideas with Execution

Distinguishing Between Idea Generation and Execution

  • While having numerous ideas is valuable, candidates must also demonstrate clarity and execution skills. The ideal candidate balances creativity with practicality in delivering clear designs.

Avoiding Scatterbrained Approaches

  • Candidates who present many ideas but fail at execution due to poor time management or focus are not suitable hires. Effective design requires thoughtful execution alongside innovative thinking.

Emphasizing Playfulness in Design Process

  • The speaker advocates for a playful approach to product development, contrasting it with rigid methodologies that may not align with their company's culture. Play fosters creativity and innovation.

Audience Questions: Learning from Failures

Spectacular Failures in Adopting New Methods

Understanding Momentum in Business

The Challenge of Change

  • Discusses the difficulty businesses face when trying to implement rapid changes, emphasizing that momentum from past practices influences current operations.
  • Explains how larger companies move slowly due to their mass and established routines, making it hard to pivot quickly.
  • Highlights that many businesses are fundamentally flawed, with success being an outlier rather than the norm.

Analyzing Failure

  • Reflects on the complexity of business failures, suggesting that pinpointing exact reasons for failure is often elusive and subjective.
  • Compares software development to mechanistic systems, noting that software work involves numerous variables and inputs which complicate analysis.

Implementing New Strategies

  • Addresses the implementation of new methodologies like Shape Up within traditional companies, typically through smaller teams experimenting with these concepts.
  • Suggests that adopting new strategies doesn't require a full commitment; partial integration can be effective.

Evolving Perspectives on Product Development

Shifts in Company Focus

  • Shares a personal journey from focusing solely on Basecamp to recognizing the desire to create multiple products again after initially consolidating efforts.
  • Describes the decision-making process behind creating HEY.com as a response to internal desires for innovation and product diversity.

Embracing Change

  • Discusses the significant shift in company identity from 37signals to Basecamp, signaling a commitment to one primary product before expanding again.
  • Expresses an ongoing willingness to adapt opinions and approaches regularly, indicating a dynamic mindset towards product design and strategy.

Continuous Learning

The Pathless Path: Designing Life and Business Intentionally

Intentional Life Design

  • The speaker discusses the concept of designing life and business intentionally, contrasting it with the default path of building a company, raising funds, and seeking an exit.
  • Acknowledges the "pathless path" philosophy, emphasizing that while there are guiding principles, there is no pre-defined plan for their journey.

Embracing Flexibility in Business

  • The company operates without long-term plans; decisions are made every six weeks based on current circumstances rather than rigid timelines.
  • The speaker expresses comfort in not knowing the exact direction they are heading, focusing instead on intuition and personal happiness as guiding factors.

The Dangers of Long-Term Planning

  • Asserts that extensive planning can lead to misaligned decisions; obligations can create unhappiness if one feels compelled to follow through on unwanted commitments.
  • Emphasizes staying present and responsive to immediate needs rather than adhering strictly to future obligations.

Independence as a Core Value

  • Highlights the importance of independence in business decisions; choosing not to raise money allows for greater control over their work environment.
  • Discusses how independence enables them to pursue entrepreneurial goals without external pressures or expectations from investors.

Product Launch Philosophy

  • Describes a lack of predetermined success metrics when launching new products; outcomes are uncertain but embraced as part of the process.
  • Stresses that pride in their work drives them more than specific user adoption numbers or market success; they focus on creating quality products first.

Focus on Personal Satisfaction

  • While hoping for positive reception from users, the primary motivation remains personal satisfaction and pride in their creations.

Alternative Approaches to Business

The Concept of Alternatives in Business

  • The speaker expresses a dislike for the term "competition," advocating instead for providing alternatives that offer different approaches, pricing, or functionalities.
  • Emphasizes that if a product is not an alternative, it may not need to exist; pride in the work is paramount regardless of market acceptance.

Pride in Creation

  • Discusses the HEY email service and expresses pride in their work despite uncertainty about its success; emphasizes focusing on quality over speculation.
  • Mentions company principles and highlights the importance of being proud of what they create, regardless of external opinions.

Work Culture and Language

  • Introduces the principle "work isn't war" and critiques the use of war metaphors in business language which can create a negative mindset.
  • Lists common aggressive business phrases like "conquer" and "target," arguing they contribute to a depressing view of work.

Shifting Perspectives on Work

  • Questions why businesses often look to military models for inspiration, suggesting that such comparisons are inappropriate for most industries.
  • Advocates for using more positive language focused on creation rather than destruction, promoting a mindset centered around pride and excitement.

Bootstrapping Your Business

Challenges of Bootstrapping

  • Acknowledges the difficulties faced when starting a business with limited resources but emphasizes independence as a key benefit.

Practical Advice for Startups

  • Advises aspiring entrepreneurs to remain small as long as possible to maintain control over costs amidst unpredictable market conditions.
  • Encourages individuals to do as much work independently before hiring others, highlighting potential complications from bringing on additional team members.

Cost Management Strategies

  • Stresses controlling personal costs since many external factors are beyond one's control; suggests avoiding unnecessary expenses like branding or office space initially.

Don't Complicate Your Business

The Importance of Simplicity in Business

  • Avoid hiring a web designer; focus on efficiencies to keep costs low. Complexity arises when businesses overcomplicate their processes, making things harder than necessary.
  • Brian Chesky's insights highlight how companies can become overly complicated, creating a complex structure that is difficult to revert back to simplicity.
  • Acknowledging the potential for failure is crucial; even with best practices, outcomes are uncertain and may lead to setbacks.

Embracing Negative Visualization

  • At 37signals, the concept of negative visualization encourages entrepreneurs to consider the worst-case scenarios and accept them as part of the process.
  • For example, exploring new ONCE products involves risks such as market rejection or operational failures. However, being at peace with these possibilities allows for more innovative exploration.

Project Management Philosophies

  • Discussion about Linear reveals shared philosophies in project management software: growth isn't prioritized; decisions are based on instinct rather than external pressures like VC funding.
  • The conversation raises questions about whether this approach could be viable within venture capital frameworks while maintaining efficiency and thoughtful operations.

The Risks of Excess Capital

  • Having too much money can lead to inefficiencies and sloppiness in business operations since there’s less pressure to be profitable or efficient.
  • Companies often feel compelled to spend VC funds quickly on hiring and marketing without considering long-term sustainability.

The Value of Bootstrapping

  • Bootstrapping forces entrepreneurs to learn how to generate revenue effectively, honing their skills in making money rather than just spending it.
  • Just like learning an instrument requires practice, running a successful business necessitates consistent experience in generating profit. Without this practice, businesses struggle when they eventually need profitability.

Understanding Business Discipline and Constraints

The Importance of Discipline in Business

  • Emphasizes the need for discipline to succeed in business, highlighting that incentives often push companies towards spending more money and rapid growth.
  • Suggests that having constraints is crucial; without them, businesses may become complacent due to excess funding, leading to inefficiencies.

Real-World Examples of Scrappiness

  • Shares a story about Peter Rahal from RXBAR, who was advised by his father to focus on selling products directly rather than getting lost in fundraising efforts.
  • Highlights the value of scrappiness in entrepreneurship, noting that large amounts of venture capital can diminish the drive to develop essential skills like profitability.

Economic Cycles and Market Confusion

  • Discusses current economic challenges where funding is harder to secure, resulting in layoffs and confusion among companies unaccustomed to operating with limited resources.
  • Expresses empathy for businesses struggling with this transition as they lack experience navigating such financial constraints.

Personal Reflections on Growth Strategies

  • Reflects on personal experiences with managing funds and emphasizes that growing a business effectively cannot solely rely on financial backing.
  • Quotes a simple yet profound business strategy: "Just keep making great shit," underscoring the importance of maintaining quality while enjoying the work process.

Profitability Over Revenue Generation

  • Stresses that aiming for profit is more sustainable than chasing high revenue figures, citing advice received from his father: "No one ever went broke making a profit."

Introducing ONCE: A New Approach to Software Products

Concept Behind ONCE

  • Introduces ONCE as an initiative aimed at addressing subscription fatigue by offering non-SaaS software products that users can purchase outright instead of subscribing.

Critique of Subscription Models

  • Critiques traditional SaaS models where users pay monthly for software but often receive minimal updates or new features over time.

Benefits of One-Time Purchases

What is the Concept Behind Once?

Introduction to Once

  • The company plans to launch a new product with no recurring fees, offering updates and support. They aim to release three more products next year.
  • There are numerous business software commodities available, yet many charge high prices despite having similar functionalities.

Identifying Market Opportunities

  • The speaker highlights the lack of price differentiation in business software, likening it to generic products in other industries.
  • The goal is to create high-quality, essential generics that focus on core functionalities (the 80-20 rule), developed quickly and with minimal maintenance costs.

Product Launch Plans

  • The first product being relaunched is Campfire, an early group chat tool originally launched in 2006.
  • Campfire predates Slack and was difficult for users to understand initially; however, it has now become a commodity due to the proliferation of chat tools.

Features of Campfire

  • The relaunch will allow users to pay once for installation on their own servers, providing a simpler alternative to expensive monthly subscriptions like Slack or Teams.
  • Users may choose to use Campfire alongside existing tools as a backup or for specific secure communications within teams.

Unique Selling Points

  • Customers will receive the source code with their purchase, allowing modifications while adhering to licensing agreements.
  • This approach offers flexibility not typically found in subscription-based software models.

Accessibility and Global Reach

  • Efforts are being made to minimize language barriers by limiting text usage and providing translation options within the software interface.

Exploring New Realms in Software Development

The Excitement of Creative Exploration

  • The speaker discusses the novelty of exploring different languages for certain words, emphasizing how new tools allow for creative play and exploration that wasn't possible with traditional SaaS models.
  • There is a growing excitement around this creative exploration, contrasting it with the speaker's previous contentment in building Basecamp. They express a desire to try something new and innovative.

SaaS vs. Alternative Models

  • While continuing to support SaaS through Basecamp, the speaker believes there should be alternatives where users can buy software instead of renting it, suggesting an interesting experiment in software distribution.
  • The traditional model of software updates is discussed; users will receive all minor updates for free but may need to purchase major upgrades at a discounted rate.

Target Market and Pricing Strategy

  • The target market is clarified as not aiming to replace Slack in large tech companies but rather focusing on smaller businesses or individuals who might find value in a one-time purchase.
  • Aiming for a price point under $1,000, the goal is to make purchasing the software an easy decision for potential customers.

Unique Selling Points

  • The product's ability to operate in air-gapped environments makes it suitable for high-security facilities, which could attract niche markets despite being small.
  • Historical context is provided about past interest from secure organizations like the White House, highlighting the unique security features of their software.

Release Timeline and Future Plans

  • A tentative release timeline indicates that by mid-December 2023, they plan to roll out the first batch of customer access while refining any issues before broader availability.
  • Although there was hesitation about promising specific dates due to past experiences, they are optimistic about meeting their end-of-year deadline.

Final Thoughts Before Conclusion

Understanding Simplicity in Business

The Complexity of Success

  • Humans often complicate simple concepts; significant progress can be made with just two people working together over short periods.
  • Success does not require being a large company or raising substantial funds; profitability and customer acquisition are achievable on a smaller scale.
  • Contrary to popular belief, having more money can complicate matters due to increased expectations and loss of scrappiness.
  • It's essential to consider the "strings attached" when acquiring resources, as they may limit operational flexibility.

Recommended Reading for Clarity and Creativity

  • A highly recommended book is Several Short Sentences About Writing by Verlyn Klinkenborg, praised for its focus on sentence structure and clarity in writing.
  • Derek Sivers' Hell Yeah Or No is another favorite, emphasizing decision-making clarity through the concept of enthusiastic commitment versus indifference.
  • The book Home-made: Contemporary Russian Folk Artifacts showcases ingenuity born from necessity, highlighting creative problem-solving in resource-limited situations.

Insights on Ingenuity and Resourcefulness

  • The book features stories of individuals creating solutions from everyday items, illustrating the beauty of human creativity under constraints.
  • Examples include innovative uses for common objects like turning forks into TV antennas or crafting door handles from available materials.

Personal Preferences in Media Consumption

Favorite Movies and Shows

  • While generally not a consumer of television or movies, the speaker enjoyed watching Oppenheimer, appreciating its theatrical experience.

Interviewing Techniques

  • A preferred interview question involves asking candidates what they would pursue if given more time with their ideas, revealing their passions and priorities.
  • Another insightful question focuses on whose work candidates admire, providing insight into their inspirations and values within their field.

Understanding Candidate Perspectives

Exploring the Joy of Driving and Business Metaphors

Rediscovering the Analog Driving Experience

  • The speaker shares their recent love for driving stick shift cars, highlighting a nostalgic return to an analog driving experience that fosters a deeper connection with the vehicle.
  • They draw parallels between this experience and their business approach, describing their company as having a "stick shift" model—direct and straightforward without unnecessary complexities.
  • In contrast, large businesses are likened to automatic transmissions, where there is a disconnect from the actual work due to layers of abstraction and simulation.
  • The speaker emphasizes the beauty in both driving styles but notes that modern cars lack the direct feel that enhances engagement with the driving process.
  • They advocate for staying connected to one's work, suggesting that this directness adds significant value in both driving and business contexts.

Life Motto: Worry Less

  • The speaker reflects on a life motto inspired by Tom Petty's lyrics: "Most of the things you worry about never happened anyway," emphasizing its truthfulness in daily life.
  • They express how excessive worrying often leads to unnecessary stress over events that turn out fine, encouraging others to adopt a similar mindset in business decisions.
  • This philosophy promotes focusing on present actions rather than future anxieties, reinforcing resilience against potential setbacks or failures.

Upcoming Book on Intuition in Business

  • The speaker discusses plans for a new book centered around gut feelings and intuition in decision-making within business contexts.
  • They argue that many existing business books overlook these aspects, favoring measurable metrics instead; they aim to celebrate intuition as an essential tool for effective decision-making.
  • The book will explore various applications of intuition across different areas such as hiring and product development while reflecting on past decisions made using gut instinct.

Insights from Charlie Munger

  • A discussion about human misjudgment leads into reflections on insights gained from Charlie Munger regarding creativity stemming from ignorance about established methods.
  • The speaker recalls asking Munger whether being ignorant can empower one’s creativity; Munger affirmed trusting instincts can lead to innovative outcomes.

The Importance of Following Your Gut

Confidence in Decision-Making

  • The speaker emphasizes that feelings and instincts are crucial when making decisions, especially in the absence of evidence or examples to guide actions.
  • This perspective instills confidence and hope, suggesting that trusting one's gut can lead to meaningful outcomes.
  • The speaker reflects on how this idea may have inspired their book, highlighting the significance of intuition in creative processes.

Engaging with the Audience

  • Jason Fried shares his contact information for listeners who wish to reach out: he is available on X (formerly Twitter), LinkedIn, and via email at Jason@hey.com.
  • He encourages audience engagement by inviting questions and discussions about his work.

Organic Growth Through Word of Mouth

  • Fried discusses the importance of organic growth for his business, noting that they do not heavily invest in advertising or marketing.
Video description

Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss: • Why he and his team prioritize profit above all else • The unexpected challenges with raising venture capital • The “Shape Up” framework for building products • Why, and how, to foster a gut-driven culture • Jason’s thoughts on why work should not feel like war • Advice for starting a bootstrapped business • The philosophy behind Once, 37signals’s new line of software products — Brought to you by Coda—Meet the evolution of docs: https://coda.io/lenny | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=accelerate | Wix Studio—The web creation platform built for agencies: https://www.wix.com/studio?utm_source=Lennyspodcast&utm_medium=Podcastad&utm_campaign=SL Find the transcript and references at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking Where to find Jason Fried: • X: https://twitter.com/jasonfried • LinkedIn: https://www.linkedin.com/in/jason-fried/ • Email: jason@hey.com Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Jason’s background (03:49) The success of 37signals (06:46) When raising money makes sense (09:58) The power of small teams (13:55) Defining success and goals (17:08) Playing “infinite games” in life (20:11) Starting a business vs. staying in business (22:13) Lessons from 25 years in business (27:28) Venture scale vs. bootstrapping (30:30) Choosing the right path for your business (33:19) The “Shape Up” framework (37:59) The drawback of promises (39:56) Adopting a new way of working (41:36) The two-week cooldown (43:53) Trusting intuition and gut (46:41) Creating a gut-driven culture (49:44) What Jason looks for in new hires (56:19) Advice on making changes and adapting (01:00:06) What Jason has changed his mind about (01:02:33) Planning in 6-week stretches and figuring it out as you go (01:06:43) Being proud of the work you do (01:09:05) Jason’s thoughts on why work should not feel like war (01:11:31) Advice for starting a bootstrapped business (01:14:33) You must be at peace with the worst that can happen (01:15:42) The benefits of bootstrapping (01:19:11) The value of constraints in business (01:22:00) Jason’s philosophy: “Just keep making great shit” (01:23:19) Once, 37signals’s new line of software products (01:26:33) The philosophy behind Once (01:35:47) Closing thoughts (01:37:23) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.