Matthew B. | Leland

Matthew B.

5.0

(5)

Former VC & Startup CEO | Strategy, Fundraising & Pitch Deck Expert

Studied at Harvard University

Works at Trinket Inc

Successful clients at

Available tomorrow at 2:00 PM UTC

Protected by the Leland Experience Guarantee

Available tomorrow at 2:00 PM UTC

Questions? Start chatting with this coach before you get started.

Matthew's Coaching Offerings

Custom hourly · $200/hr

Get help with Interview Prep, Market Research, and .

Matthew also coaches for Startups, MBA, and Private Equity. View all.

Matthew’s Business Operations & Strategy Qualifications

Coaches professionally

Experience level: Executive

10+ people coached for Business Operations & Strategy

I’m a former VC where I evaluated hundreds of founders, reviewed pitch decks, built investment theses, and led diligence for both private and public investments. I later became the CEO and founder of a venture-backed startup funded by Silicon Valley and Singapore-based VCs, giving me firsthand experience building strategy, GTM plans, and fundraising materials from the founder side. My background includes 20 years in strategy, finance, and operations across roles at Catcha Group (Southeast Asia’s leading venture builder) and the Clermont Group (private equity). I specialize in helping early-stage companies clarify their business model, craft investor-ready narratives, and structure compelling pitch decks and strategic plans. Whether you need to refine your fundraising story, tighten your strategy, or build a clear and persuasive pitch, I bring the perspective of both an investor and a founder to help you communicate your value and accelerate your growth.

Matthew can help with:

Interview Prep

Market Research

Operations Management

LinkedIn Review

Competitive Analysis

Business Strategy Development

Cover Letters

Resume Review

Project Management

Financial Analysis

Negotiation Skills

Matthew also coaches for Startups, MBA, and Private Equity. View all.

About Matthew

I’m a former VC, and CEO/founder of a venture-backed startup. I’ve spent 20 years in finance, strategy, and investing where I've been evaluating hundreds of founders, reviewing pitch decks, leading diligence, and writing investment materials that were used to raise millions. I hold an MBA from MIT, an MPA from Harvard, and a BA from Dartmouth, where I graduated with honors (and served as an alumni interviewer). My specialty is helping people win high-stakes opportunities through narrative and strategy. For founders, I refine pitch decks, investor narratives, business plans, and GTM strategies. For MBA/MPA/college applicants, I help craft compelling essays, shape positioning, and communicate their value with precision. I combine investor-level insight, founder experience, and elite storytelling skills to help clients communicate clearly, persuasively, and powerfully whether you’re pitching investors or applying to top programs.

Why do I coach?

Pitch Decks & Fundraising (Founders) -Complete pitch deck creation and refinement -Investor narrative positioning -Business model & traction storytelling -Fundraising strategy & investor readiness -Market sizing + competitive landscape analysis -Financial model review & messaging -Pre-seed to Series A preparation Business Strategy Consulting -Early-stage strategy and GTM planning -Business plan review and development -Monetization + revenue model refinement -Founder coaching for investor communications -Competitive analysis & differentiation MBA / MPA / College Admissions Strategy -Narrative positioning & essay strategy - Application storytelling (MBA, MPA, MPP, undergrad) - Full essay edits + structural rewrites - Coaching for elite business/public policy programs - Former Dartmouth Alumni Interviewer insights - Extensive experience advising international + Southeast Asian applicants

Work Experience

Co-Founder, Co-CEO

Trinket Inc

August 2022 - Present

Trinket is the fanbase OS. We use AI to help anyone and anything with a fanbase generate far more revenue than they could by themselves. Specifically, we sell limited-edition, personalized, and authenticated collectibles. Our core innovation is the control of both the primary and secondary markets. This dual control means creators capture more value up front and share in resale upside - they receive royalties on merch resales.

Partner

Turret Capital

July 2017 - April 2022

Turret Capital is a global biomedical investment and venture-building company. Headquartered in New York and with a presence in Asia, we maintain an international outlook to identify opportunities to help patients across the world.

Head of Fund Investments

Catcha Group

February 2016 - June 2017

Catcha Group is one of Southeast Asia’s most established technology investment platforms with a venture building record consisting of 6 IPOs and over US$1 billion in value creation. - Worked directly with the CEO to identify new markets for venture building endeavors across Southeast Asia - As a member of the Investment Committee, reviewed and voted on every investment decision made by the firm

VIce President

Catcha Group

August 2014 - February 2016

-Charted and set venture capital investment approach for firm’s activities across the region and targeted financing rounds that ranged from seed to series C -Discovered, evaluated, and conducted diligence on startups in the fin-tech, e-commerce, enterprise, and on-demand verticals in Thailand, Singapore, Vietnam, Indonesia, Malaysia, the Philippines, Myanmar, and Hong Kong -Led deep integration and company outreach efforts across the ASEAN tech ecosystem

Special Situations

Clermont Group

August 2013 - August 2014

The Clermont Group is a multibillion-dollar investment group founded by value investor Richard Chandler -Reporting to CEO, held principal responsibility for review and oversight of a private equity portfolio and illiquid public markets portfolio spanning six firms in four countries -Evaluated prospectuses and presented recommendations for private and public investments to CEO and Chairman -Opposite senior management, conducted intensive due diligence and financial analysis on a major Chinese energy joint venture -Held responsibility for training junior associates in valuation principles and DCF modeling Selected Transactions, Investments, and Due Diligence: -Evaluation of equity injections to made be annually to Sinopec Green Energy, Orka Geothermal’s China JV with Sinopec -Analysis of >$100mm of debt and equity investments to build Orka’s new geothermal business line in the Philippines -Analysis of a Southeast Asia hospital bolt-on acquisition to add to an existing healthcare portfolio company -Evaluation of shareholder engagement and investment strategy regarding a $130mm purchase of Energy World Corporation shares

Founder and Executive Director

pixel equity

February 2009 - May 2010

First 501(c)(3) NGO to provide video game technology to low-income children -Launched the first non-profit organization that provides video game technology access to underserved children in school systems and youth programs in New York, San Francisco, Chicago, and Atlanta -Designed and implemented a nationwide market maker and exchange for used and new video games that are matched with after-school and summer programs targeting disadvantaged youth -Created a transparent system of tracking financial contributions that allows donors to make micro-transactions and fractional payments -Managed the creation of a proprietary Facebook app that displays donors’ badges on their profiles reflecting the amounts of money they have contributed and the youth centers to which they have given -Coordinated press efforts and served as primary spokesman for interviews by “New York One” news station, San Jose Mercury News, The Globe and Mail, and the Toronto Star