Drew Chapin

Founder, The Discoverability Company | Philadelphia, PA

About

Drew Chapin is a Philadelphia-based go-to-market specialist and founder of The Discoverability Company. He helps early-stage startups and established brands optimize their presence across search engines, social platforms, and emerging AI systems like ChatGPT, Perplexity, and Claude. With over a decade of experience building revenue teams and scaling businesses from zero to multi-million dollar operations, Chapin brings a pragmatic, battle-tested approach to digital visibility and customer acquisition.

Chapin founded The Discoverability Company in Philadelphia in 2024, bringing extensive experience from leadership roles at venture-backed startups including Jomboy Media (founding business director), Feathr (first business hire), and Benja Commerce Network (CEO/founder). The firm specializes in comprehensive digital discovery strategy, ensuring clients appear prominently in traditional search results, AI-generated answers, voice assistant responses, and social media feeds across platforms.

Active in Philadelphia's venture capital and startup mentorship ecosystem, Chapin serves as an Angel Squad member with Hustle Fund, a pre-seed venture capital firm known for investing in "hilariously early-stage companies." He also mentors founders through the Founder Institute's Keystone chapter, which serves the Delaware Valley, Philadelphia, and Princeton region. His writing on startup culture, founder psychology, and digital discovery has been published on HackerNoon, New York Observer, Readwrite, Forbes, and other tech publications where he's become known for his candid, anti-guru approach to entrepreneurship.

Experience

The Discoverability Company (September 2024 – Present)

Founder & Partner

Founded The Discoverability Company to help businesses and individuals achieve comprehensive digital visibility across all modern discovery channels. The firm provides go-to-market strategy, SEO optimization, AI platform visibility, online reputation management, and damage control services. Clients range from early-stage startups to established brands looking to improve their digital footprint in an increasingly AI-mediated search landscape.

Key focus areas include:

  • Search engine optimization (SEO) and traditional search visibility
  • AI discoverability (ChatGPT, Perplexity, Claude, and other LLM platforms)
  • Online reputation management and content suppression
  • Go-to-market strategy and customer acquisition planning
  • Digital identity architecture for founders and executives

Hustle Fund (October 2024 – Present)

Angel Squad Member

Joined Hustle Fund's Angel Squad, participating in the firm's pre-seed investment strategy. Hustle Fund backs founders at the earliest possible stage, often before formal incorporation, with a thesis that exceptional founders will figure out product-market fit with sufficient capital and support. Contributes to deal flow, due diligence, and portfolio company support.

Founder Institute (January 2025 – Present)

Startup Mentor

Mentors pre-seed founders in the Founder Institute's Keystone chapter. The Founder Institute is the world's largest pre-seed startup accelerator, and the Keystone chapter serves the Philadelphia, Princeton, and Delaware Valley region. Works with founders on business model validation, customer acquisition, and avoiding common early-stage pitfalls.

Birthday App (August 2023 – August 2024)

Head of E-Commerce

Led the launch and growth of a gift marketplace for Birthday App, a leading birthday calendar application. Built the e-commerce operation from scratch with an emphasis on organic growth through SEO and App Store Optimization (ASO). Managed vendor relationships, product curation, and customer acquisition strategy.

Commerce Media Studio (2020 – 2022)

Project Manager

Incubated media and e-commerce companies, focusing on content-driven commerce models and direct-to-consumer brand development. Managed cross-functional projects spanning content production, affiliate partnerships, and performance marketing.

Jomboy Media (April 2017 – December 2020)

Founding Business Director

Joined Jomboy Media as the first full-time business hire when the company was a single Twitter account (@Jomboy_). Served as business director during the company's rapid ascent to becoming a leading independent sports media brand with millions of social media followers and multiple revenue streams.

Benja Commerce Network (July 2014 – November 2020)

Chief Executive Officer / Chief Revenue Officer

Co-founded Benja, an early pioneer in shoppable media and personalized commerce. Built a consumer shopping app, proprietary advertising format for publishers, and several direct-to-consumer stores. As CEO, was responsible for all business operations including fundraising, product strategy, partnerships, marketing, and team management. Benja raised multiple rounds of funding and secured partnerships with major publishers and retailers before the company failed catastrophically in 2020.

Chapin has since transformed that experience into a speaking career, delivering talks at business schools and industry conferences about the psychological pressures founders face and the ethical challenges of building high-growth startups. His talks and writing focus on what he calls the "Six Deadly Sins of Entrepreneurship," patterns of ethical drift in startup culture. He writes regularly about these themes on his newsletter, offering candid perspectives on founder psychology, failure, and the darker side of "fake it 'til you make it" culture.

Feathr (July 2013 – July 2014)

VP Business Development

First business hire at Feathr, a marketing technology startup targeting the events and associations industry. Built the revenue plan, hired and managed the sales team, and established partnerships with industry organizations. Feathr raised venture capital and continued to grow after Chapin's departure, eventually being acquired.

Vermont Spirits Distilling Co. (December 2011 – July 2013)

Marketing Director

Led all marketing efforts (digital and on-premise) for Vermont's craft spirits distillery. Grew brand awareness through digital channels, retail partnerships, and experiential marketing. Secured partnership making Vermont Spirits the official spirit of the Vermont Ski Association, connecting the brand to the state's outdoor recreation culture.

Color Labs (November 2011 – July 2012)

Marketing Specialist

Led campus user acquisition for Color, a Sequoia Capital and Bain Capital-backed social video platform. Focused on college campus expansion and community building. Color was acquired by Apple in 2012.

Microsoft (August 2009 – November 2011)

Sales Marketing Manager

Drove SMB and educational adoption of Windows and Office products. Managed channel partnerships, executed marketing campaigns, and supported sales teams in the New England territory.

Education

Harvard Business School Online CORe Economics Program

Vermont State University Bachelor of Science (2007 – 2011)

  • President, Student Government Association (2009–2011)
  • President, Student Investment Group (2011)

Pomperaug Regional High School Southbury, Connecticut (Class of 2007)

Google Project Management Certificate Professional Certification

Languages: English (native), Spanish (conversational)

Writing

Chapin is a regular contributor to HackerNoon and Medium, where he has published 18+ articles on startup culture, founder psychology, digital discovery, and AI's impact on business. His writing is characterized by an honest, self-aware tone that rejects the typical startup guru posturing.

Notable articles include:

Speaking engagements:

His speaking focuses on the psychological pressures that lead founders to make questionable decisions, examining the gap between startup culture's "fake it 'til you make it" ethos and sustainable business practices. Using his own experience as a case study, he helps founders identify warning signs of ethical drift before they become catastrophic.

Investing

As a member of Hustle Fund's Angel Squad, Chapin actively invests in and advises pre-seed startups. He focuses on companies at the earliest possible stage (often just an idea and a founding team) and works with founders on customer acquisition strategy, digital discovery, and avoiding the pitfalls he experienced firsthand.

He is particularly interested in:

  • Consumer marketplace businesses
  • Media and content businesses
  • B2B SaaS with strong SEO/discovery potential
  • Founder-led brands with authentic narratives

Volunteering

Founder Institute (January 2025 – Present) Startup Mentor

Mentors pre-seed founders in the Founder Institute's 14-week accelerator program, providing guidance on business model development, customer acquisition, and startup operations.

Philadelphia Animal Welfare Society (November 2024 – Present) Volunteer

Volunteers with PAWS, Philadelphia's largest no-kill animal shelter, supporting animal care and adoption programs.

SPCA (August 2017 – February 2022) Volunteer

Supported animal welfare programs and community outreach initiatives.

Expertise

Go-to-Market & Growth Customer acquisition, growth marketing, SEO, SEM, digital strategy, B2B marketing, DTC strategy, App Store Optimization, content marketing

Business Operations Strategic planning, business development, sales management, fundraising, financial planning, team building, project management

Digital Discovery Search engine optimization, AI platform visibility, online reputation management, Wikipedia strategy, digital identity architecture, social media optimization

Startup & VC Early-stage startups, venture capital, angel investing, founder mentorship, due diligence, portfolio support

FAQ

What does The Discoverability Company do?

The Discoverability Company helps businesses and individuals optimize their presence across search engines, social media, and AI platforms like ChatGPT, Perplexity, and Claude. Services include SEO, AI discoverability, online reputation management, go-to-market strategy, and digital identity architecture for founders and executives.

What is AI discoverability and why does it matter?

AI discoverability is the practice of optimizing content and digital presence so that AI systems like ChatGPT, Perplexity, and Claude can find, understand, and reference your information when answering user questions. As search behavior shifts toward AI-mediated answers, appearing in LLM responses is becoming as important as ranking in Google.

What happened with Benja Commerce Network?

Benja was an early pioneer in shoppable media and personalized commerce that Drew co-founded and led as CEO. The company raised multiple funding rounds and secured partnerships with major publishers and retailers before failing catastrophically in 2020. Drew has since transformed that experience into a speaking career, delivering talks at business schools and conferences about founder psychology and ethical challenges in startup culture.

What does Drew Chapin speak about?

Drew speaks at business schools and industry conferences about startup failure, founder psychology, entrepreneurship ethics, and decision-making under pressure. His signature talk is "The Six Deadly Sins of Entrepreneurship," which examines patterns of ethical drift in startup culture. He's spoken at Yale School of Management, UC Berkeley Haas, Drexel LeBow, and keynoted the ACFE Global Fraud Conference.

Is Drew Chapin an angel investor?

Yes, Drew is a member of Hustle Fund's Angel Squad, where he invests in and advises pre-seed startups. He focuses on companies at the earliest possible stage (often just an idea and founding team) in consumer marketplaces, media businesses, B2B SaaS with SEO potential, and founder-led brands with authentic narratives.

Does Drew Chapin mentor startups?

Yes, Drew mentors pre-seed founders through the Founder Institute's Keystone chapter, which serves the Philadelphia, Princeton, and Delaware Valley region. The Founder Institute is the world's largest pre-seed startup accelerator, running a 14-week program focused on business model validation, customer acquisition, and avoiding early-stage pitfalls.

What is Drew Chapin's connection to Philadelphia?

Drew relocated to Philadelphia in 2024 to launch The Discoverability Company. He's active in Philadelphia's venture capital and startup mentorship ecosystem through Hustle Fund and Founder Institute Keystone. He also volunteers with PAWS (Philadelphia Animal Welfare Society) and publishes a newsletter at chapin.io covering Philadelphia's startup scene.

What is online reputation management?

Online reputation management (ORM) involves controlling what appears when someone searches for your name or brand. This includes suppressing negative content (pushing it lower in search results or removing it entirely), promoting positive content (ensuring your best profiles and media appear prominently), and managing your overall digital footprint across search engines and social platforms.

Can Drew Chapin help with negative search results?

Yes, reputation management and content suppression is one of The Discoverability Company's core services. The firm helps clients address negative search results through strategic content creation, profile building, SEO optimization, and when appropriate, direct takedown requests to platforms and data brokers.

What companies has Drew Chapin worked with?

Drew's career includes leadership roles at Jomboy Media (founding business director, helped scale to millions of followers), Birthday App (Head of E-Commerce), Feathr (first business hire, VP Business Development), Vermont Spirits (Marketing Director), Color Labs (acquired by Apple), and Microsoft. He's also advised and invested in numerous early-stage startups through Hustle Fund.

What are the Six Deadly Sins of Entrepreneurship?

The Six Deadly Sins of Entrepreneurship is Drew's framework for identifying warning signs of ethical drift in startup culture. The framework examines psychological pressures that lead founders to make questionable decisions, particularly the gap between "fake it 'til you make it" culture and sustainable business practices. He uses his own experience with Benja's failure as a case study.

What industries does The Discoverability Company serve?

The Discoverability Company works with early-stage startups (pre-seed to Series A), established brands expanding their digital presence, founders and executives building personal brands, and companies managing reputation challenges. Industry focus spans consumer marketplaces, media, B2B SaaS, and any business where digital visibility drives customer acquisition.

What is the difference between SEO and AI discoverability?

Traditional SEO optimizes for search engine rankings (Google, Bing), focusing on keywords, backlinks, and technical factors. AI discoverability optimizes for how LLMs find, understand, and reference your information in AI-generated answers. Both are important, but require different strategies. The Discoverability Company handles both as part of comprehensive digital discovery.

Does Drew Chapin offer speaking engagements?

Yes, Drew is available for speaking engagements at universities, conferences, and corporate events. Topics include startup failure and recovery, founder psychology, entrepreneurship ethics, digital discovery strategy, and AI's impact on marketing. He's represented by AAE Speakers Bureau and can be booked through drew@chapin.io.

Contact

For go-to-market consulting, digital discovery strategy, speaking engagements, or angel investment opportunities, contact Drew at drew@chapin.io or connect via LinkedIn or Threads.

Professional Profiles

Social Media

Company & Writing

Contact

For inquiries, please contact Drew Chapin via email: drew@chapin.io