A digestible deep-dive into how to create a better work-life. ​ By Claire Wasserman​
​ Hey Reader,
My client “K” has everything it takes to succeed as an entrepreneur. She thrives in uncertainty, makes order out of chaos, loves juggling a gazillion, embraces failure, and is continually pushing herself to try new things and learn.
The only thing is, she doesn’t have a business idea. Plus, she currently gets a great paycheck at someone else’s (not-so-great) company.
So without a product, a problem to solve, or even an idea of the kind of person she wants to serve, she’s an entrepreneur without… an enterprise.
I’ve met a lot of people like “K”, and maybe you’re one of them. Someone with the personality and desire to be your own boss, but without the steps to figure out what that means and how to get there.
This newsletter and the next one are dedicated to showing you how to do just that.
First, we’ll go over entrepreneurial types with an assessment to help identify which one you are plus a seven-day action plan to help you discover your type. Each day of this plan includes structured activities to help you explore different aspects of your entrepreneurial identity, from self-assessment and strength analysis to real-world research and opportunity mapping.
In Part 2 (so next week’s newsletter), we’ll take that info and go deeper into different business directions, what they require, and which are best suited for who you are and what you need to build a better-work life.
As always, thank you. I couldn’t be an entrepreneur without you
x Claire
PS Want to read past issues? You’re in luck – you can access them here. Just look for the lock icon and use the email you registered with (you only need to log in once.)
Your Entrepreneurial Type
Knowing your entrepreneurial type is a powerful first step in your business journey. Your natural tendencies, strengths, and motivations significantly influence which business paths will be most fulfilling and successful for you.
Just as every person has a unique fingerprint, each entrepreneur has distinctive patterns in how they create value and approach business challenges. Some naturally excel at innovation, others at building systems, while some thrive through deep expertise or community connections.
When you build a business aligned with your entrepreneurial type, you operate from a position of strength. You’ll find yourself energized rather than drained, making decisions that feel natural rather than forced. You’ll also be better equipped to anticipate potential blind spots and build complementary partnerships where needed.
Plus, understanding these patterns will guide you toward business opportunities where your natural abilities create the greatest advantage, making your entrepreneurial journey both more successful and more satisfying.
The following are twelve types of entrepreneurs with an assessment to find out which(s) you are! After you take the assessment, stay tuned for next week’s newsletter Part 2 which includes an overview and assessment that will help you explore specific business directions aligned with your unique entrepreneur type.
Just a heads up: most successful entrepreneurs embody aspects of multiple types, with one or two serving as primary drivers so don’t feel like you have to “be” just one!
Core Characteristics:​ The Innovator is driven by creating novel solutions and approaches that challenge the status quo. They possess a natural curiosity and creativity that leads them to question existing products, services, and systems. Innovators thrive when solving complex problems that others might avoid and are energized by the process of ideation and experimentation.
Natural Strengths:
Creative thinking and ability to envision what doesn’t yet exist
Comfort with uncertainty and ambiguity
Technical aptitude and quick learning in new domains
Ability to see connections and possibilities others miss
Persistence in the face of obstacles
Potential Challenges:
May struggle with the practical aspects of implementation
Can become more interested in the next new idea than finishing current projects
Might prioritize innovation over market needs or commercialization
Can find routine business operations tedious
May underestimate time and resources needed to bring innovations to market
Business Approach:​ Innovators build businesses centered around novel products, services, or methodologies. They excel at identifying unmet needs and creating original solutions. Their ventures are often characterized by intellectual property, unique approaches, and disruptive potential.
Typical Ventures:
Technology startups
Product invention and design firms
Research and development consultancies
Businesses based on proprietary methodologies or systems
Companies that reinvent traditional industries
2⃣ The Craftsperson
Core Characteristics:​ The Craftsperson is deeply committed to quality, mastery, and the tangible expression of their skills. They take immense pride in their work product and are driven by the pursuit of excellence in their chosen craft. Craftspersons value tradition, technique, and attention to detail, often creating products or services that stand out for their exceptional quality.
Natural Strengths:
Technical expertise and skill mastery
Meticulous attention to detail
Commitment to quality standards
Deep product knowledge and material understanding
Patience and perseverance in perfecting their craft
Potential Challenges:
May struggle to scale beyond personal production capacity
Could overfocus on perfection at the expense of timeliness or profitability
Might resist delegation or standardization
Can undervalue their work or charge too little
May face challenges balancing artistic integrity with market demands
Business Approach:​ Craftspersons build businesses that showcase their expertise and commitment to exceptional quality. They often maintain close personal involvement in production or service delivery and build loyal customer bases who appreciate and value their dedication to excellence.
Typical Ventures:
Artisanal or handcrafted product businesses
Specialized service providers
Custom manufacturing or production
Fine arts or creative studios
Specialty food or beverage production
3⃣ The Opportunity Spotter
Core Characteristics:​ The Opportunity Spotter has a keen eye for identifying market gaps, emerging trends, and unfulfilled needs. They excel at recognizing potential before others and acting swiftly to capitalize on it. These entrepreneurs are constantly scanning the environment for possibilities and can quickly connect dots between different trends, needs, and potential solutions.
Natural Strengths:
Market awareness and trend recognition
Quick decision-making and action orientation
Adaptability and comfort with change
Risk assessment and opportunity evaluation
Timing—knowing when to enter or exit markets
Potential Challenges:
May jump between opportunities too quickly
Could overestimate market potential
Might face “shiny object syndrome” and lose focus
May struggle with long-term operational commitment
Can overlook details in their enthusiasm for the big picture
Business Approach:​ Opportunity Spotters create businesses that capitalize on timing and market positioning. They excel at entering emerging markets, bringing successful concepts to new territories, or pivoting existing resources to meet changing demands. Their ventures are often characterized by agility and responsiveness to market conditions.
Typical Ventures:
Import/export businesses
Trend-based retail or e-commerce
Market arbitrage ventures
Early adoption of franchise concepts
Businesses that rapidly respond to emerging needs
4⃣ The Systems Builder
Core Characteristics:​ The Systems Builder excels at creating order from chaos through efficient processes, frameworks, and operations. They think in terms of workflows, scalability, and optimization. Systems Builders find satisfaction in creating repeatable processes that function smoothly and predictably, allowing for consistent results and growth without constant personal oversight.
Natural Strengths:
Analytical thinking and logical problem-solving
Process design and optimization
Organizational abilities and structure creation
Efficiency-focused mindset
Documentation and standardization skills
Potential Challenges:
May prioritize systems over customer experience
Could create unnecessary complexity
Might struggle with the human elements of business
Can be perceived as inflexible or overly procedural
May overlook creativity in pursuit of standardization
Business Approach:​ Systems Builders create ventures that leverage repeatable processes, scalable operations, and efficient delivery models. Their businesses typically feature strong operational foundations that can grow beyond the founder’s direct involvement. They excel at turning concepts into predictable, replicable business models.
Typical Ventures:
Franchise development and operations
Scalable service businesses
Process consulting or implementation firms
Operations-focused technology companies
Businesses with complex logistics or delivery requirements
5⃣ The Connector
Core Characteristics:​ The Connector thrives on relationships, networks, and bringing people together. They possess exceptional social intelligence and an ability to understand the needs and capabilities of diverse individuals and groups. Connectors create value by facilitating meaningful interactions, partnerships, and exchanges between others.
Natural Strengths:
Exceptional interpersonal and communication skills
Large, diverse professional networks
Ability to identify mutually beneficial relationships
Social intuition and emotional intelligence
Trust-building and relationship maintenance
Potential Challenges:
Business may become too dependent on personal relationships
Can struggle with systematizing relationship value
Might prioritize relationships over profitability
May find it difficult to scale beyond personal connections
Can be challenged by quantifying their impact
Business Approach:​ Connectors build businesses that leverage relationships and networks. Their ventures often create platforms, marketplaces, or services that bring together different stakeholders who can benefit from each other. They excel at creating ecosystems of value exchange.
Typical Ventures:
Networking platforms or communities
Matchmaking or recruitment services
Business development consultancies
Industry connectors or brokers
Marketplace or platform businesses
6⃣ The Expert Authority
Core Characteristics:​ The Expert Authority possesses deep knowledge and specialized expertise in a specific domain. They have invested significantly in developing their understanding and capabilities in their field. Expert Authorities build businesses based on their credibility, thought leadership, and ability to solve complex problems or provide insights that others cannot.
Natural Strengths:
Deep domain knowledge and specialized expertise
Credibility and professional reputation
Analytical and critical thinking
Problem-solving within their domain
Continuous learning and knowledge development
Potential Challenges:
May struggle to delegate as the face of the business
Could have difficulty translating expertise into business systems
Might focus too narrowly on technical details rather than customer needs
Can undervalue non-expertise aspects of business success
May resist evolution or pivoting outside their core expertise
Business Approach:​ Expert Authorities build businesses centered around their specialized knowledge and insights. Their ventures often focus on helping clients solve complex problems or achieve results through applied expertise. They typically position themselves as trusted advisors, educators, or specialized service providers.
Typical Ventures:
Professional services or consulting firms
Specialized advisory practices
Expert-led training or education businesses
Technical or specialized service providers
Thought leadership platforms
7⃣ The Social Entrepreneur
Core Characteristics:​ The Social Entrepreneur is motivated primarily by creating positive change in society or the environment. They measure success beyond financial returns, focusing on impact metrics and mission fulfillment. Social Entrepreneurs build businesses that address unmet social needs, environmental challenges, or community development while maintaining financial sustainability.
Natural Strengths:
Strong sense of purpose and mission
Ability to engage and inspire others around a cause
Creative problem-solving for social challenges
Stakeholder management and community building
Balancing financial and impact considerations
Potential Challenges:
May struggle with the financial sustainability aspects of social enterprise
Could face tension between profit needs and social mission
Might find it difficult to scale impact while maintaining quality
Can experience burnout from emotional investment in mission
May encounter skepticism from both business and nonprofit sectors
Business Approach:​ Social Entrepreneurs create ventures where social or environmental impact is integrated into the core business model. Their businesses often feature innovative approaches to addressing social challenges while generating sustainable revenue. They excel at creating multiple forms of value beyond profit.
Typical Ventures:
B Corps and social enterprises
Sustainable product companies
Community development initiatives
Environmental solution providers
Inclusive employment models
8⃣ The Growth Driver
Core Characteristics:​ The Growth Driver is ambitious, metrics-focused, and aims to build businesses of significant scale. They are energized by expansion, increasing market share, and building substantial organizations. Growth Drivers are comfortable with the challenges of rapid scaling and typically seek external investment to fuel expansion.
Natural Strengths:
Strategic thinking and big-picture vision
Comfort with rapid growth and change management
Financial acumen and metrics focus
Team building and leadership
Fundraising and investor relations
Potential Challenges:
May sacrifice quality or culture for growth
Could prioritize vanity metrics over sustainable business fundamentals
Might create unsustainable cash flow dynamics
Can struggle with the human aspects of rapid organizational change
May face burnout from constant pressure to scale
Business Approach:​ Growth Drivers build businesses designed for substantial scale from the outset. Their ventures typically feature scalable models, significant market potential, and structures that can accommodate rapid expansion. They excel at building organizations rather than simply running operations.
Typical Ventures:
Venture-backed startups
High-growth technology companies
Disruptive business models with large TAM
Roll-up strategies in fragmented industries
Platform businesses with network effects
9⃣ The Portfolio Builder
Core Characteristics:​ The Portfolio Builder creates and manages multiple business interests simultaneously. They think in terms of diversified risk, synergies between ventures, and asset allocation. Portfolio Builders are comfortable dividing their attention across different businesses and excel at seeing connections between seemingly unrelated opportunities.
Natural Strengths:
Risk management through diversification
Strategic resource allocation
Pattern recognition across different industries
Delegation and team empowerment
Financial analysis and portfolio management
Potential Challenges:
May spread attention too thin across ventures
Could struggle with depth of involvement in any single business
Might face challenges in maintaining focus
Can underestimate management requirements across multiple businesses
May find it difficult to build cohesive teams in each venture
Business Approach:​ Portfolio Builders create a collection of businesses or investments rather than focusing on a single venture. Their approach typically involves strategic ownership, partnerships, or investments across diverse business interests. They excel at managing risk while maximizing overall portfolio returns.
Typical Ventures:
Multiple complementary small businesses
Investment portfolios with active management
Holding companies
Serial entrepreneurship with overlapping ventures
Diversified passive and active income streams
The Lifestyle Entrepreneur
Core Characteristics:​ The Lifestyle Entrepreneur prioritizes personal freedom, flexibility, and quality of life in their business decisions. They create ventures that support their desired lifestyle rather than maximizing growth or profit. Lifestyle Entrepreneurs build businesses that integrate with their personal interests and allow them to maintain control over their time and location.
Natural Strengths:
Work-life integration and balance
Focus on efficiency and necessary processes
Personal passion and authentic business connection
Self-motivation and independence
Clear boundaries and priorities
Potential Challenges:
May limit business growth to maintain lifestyle preferences
Could undercapitalize the business
Might face difficulty separating personal and business identities
Can struggle with delegating or team building
May find scaling challenging while maintaining lifestyle benefits
Business Approach:​ Lifestyle Entrepreneurs build businesses that accommodate their desired way of life. Their ventures often feature flexibility, location independence, or integration with personal interests. They excel at creating sustainable businesses that serve their life goals rather than the other way around.
Typical Ventures:
Location-independent online businesses
Consultancies with flexible schedules
Passion-based service businesses
Seasonal or part-time ventures
Low-overhead, high-margin businesses
1⃣ 1⃣ The Turnaround Specialist
Core Characteristics:​ The Turnaround Specialist thrives in challenging situations and excels at fixing broken businesses or systems. They have a talent for identifying core issues in struggling organizations and implementing effective solutions under pressure. Turnaround Specialists are energized by crisis management and creating order from chaos.
Natural Strengths:
Diagnostic abilities for business problems
Decision-making under pressure
Resource optimization and efficiency improvement
Crisis management and stakeholder communication
Strategic restructuring and prioritization
Potential Challenges:
May seek out unnecessarily difficult situations
Could become bored with stable, functional businesses
Might develop a reputation tied to crisis rather than growth
Can struggle with the transition from recovery to normal operations
May focus on short-term fixes over long-term sustainability
Business Approach:​ Turnaround Specialists build businesses focused on rehabilitating struggling ventures or providing intervention services. Their approach typically involves identifying core issues, implementing rapid improvements, and creating sustainable recovery plans. They excel at creating value from distressed assets or situations.
Typical Ventures:
Business acquisition and turnaround
Restructuring consultancies
Interim management services
Distressed asset management
Crisis intervention specialists
1⃣ 2⃣ The Local Maven
Core Characteristics:​ The Local Maven is deeply connected to their geographic community and builds businesses that serve local needs. They possess intimate knowledge of local preferences, relationships, and market dynamics. Local Mavens create ventures that become integral parts of community fabric and often serve as hubs for local connection.
Natural Strengths:
Deep local market knowledge and community connections
Strong customer loyalty and relationship building
Community reputation and trust
Local supply chain and resource knowledge
Cultural understanding and local relevance
Potential Challenges:
Geographic limitations to growth
Vulnerability to local economic conditions
May struggle with expansion to new locations
Could face increasing competition from national chains
Might find it difficult to adapt to changing community demographics
Business Approach:​ Local Mavens build businesses deeply rooted in specific geographic communities. Their ventures typically feature strong local relationships, community engagement, and adaptation to local preferences. They excel at creating businesses that become local institutions and community anchors.
The Lifestyle Entrepreneur