Shepherd is the hybrid law firm for startups. We combine AI-powered technology with experienced attorneys to deliver faster, more transparent, fixed priced legal services for early-stage startups and small businesses. To learn more, please go to https://www.yourshepherd.ai.

Infrastructure perspective from 30 years of building at scale. I help founders and investors see what they're missing, look around corners, and remove roadblocks. Background: - Built one of the early ISPs (1994) - SendGrid: Early team → IPO → Twilio acquisition - Founding team at GeoTrust → VeriSign/Symantec acquisition - 7 companies founded, multiple exits - Operated across startups, public companies, and venture studios What I Do: I bring infrastructure and operational perspective to help you see opportunities, anticipate what breaks, and scale from 1 → 3 → 10+. I help you lead by identifying and removing roadblocks—strategic and operational. I provide perspective through quick sessions, deep engagements, or ongoing partnerships—depending on what you need. Tech founders: Deep on infrastructure and operations. Non-tech founders: Technical bridge + operational guidance. Investors: Portfolio-wide perspective. → mikerowan.com

A global community of post-exit founders supporting each other on life's endless journey to find purpose, fulfillment, and meaning.

Parambil is an Al-powered knowledge platform built for tort law. Products on market include automatic case validation, medical chronologies, complaints, fact sheets and more...

Led digital product strategy and innovation initiatives focused on improving enterprise sales operations. Work included: • Designing AI-enabled tools and workflows to improve advisor effectiveness • Driving operational efficiency across sales platforms and internal systems • Partnering with business and technology leaders to move from concept to execution

Operations as a service for venture-backed founders. The operational & financial visibility needed to be a data-driven decision maker. We take care the business & financial operations so founders can lead their business more effectively. - Accounting & Bookkeeping - Corporate Setup & Entity Compliance - Planning & Budgets - Financial Performance Reviews - Financial & Data Room Organization - Mentor Support & Guidance

Chief Product Officer responsible for product strategy, execution, and operating discipline across Techstars’ product studio venture initiatives. Primary responsibilities: • Product strategy, roadmap, and execution across studio platform and programs • Building scalable product and operating systems supporting founders and teams • Partnering with leadership, operators, investors, and studios to drive clarity and execution This work operated at portfolio scale, balancing platform needs, founder experience, and operational discipline. Additional roles @ Techstars: • Entrepreneur in Residence (2019–2020), guiding founders w/operational & product support • Mentor (2016 - ongoing), providing guidance to early-stage companies across cohorts

Built and operated multiple product studio ventures spanning infrastructure, developer tools, and early-stage incubation. Studios included: • Stray Labs (acquired by SendGrid) — a developer & infrastructure focused studio building tools and systems-oriented products prior to SendGrid. • Joy Labs — a venture-focused studio enabling design and development of new software products and early-stage initiatives. • Hive Hatch — an early-stage investment and venture participation effort focused on structured ideation and founder support. Across these efforts: • Led product strategy and 0→1 execution across multiple concurrent initiatives • Conducted diligence and participated in early-stage opportunities • Allocated capital and operating resources across portfolio bets • Owned financial operations, P&L management, and performance visibility • Built repeatable discovery, delivery, and operating systems • Operated both as hands-on product leader and strategic decision-maker

IPO (SEND) in 2017 & later Acquired by Twilio (TWLO) Founded and led SendGrid Labs, an internal product studio focused on Product R&D (Horizon 2 & 3) in/validating next generation products for our customers to love and value. - Multi-channel marketing automation, workflows, APIs and applications - Data replication & transformation APIs and applications - Cloud-based load testing platform for APIs and applications - IOT device deployment and messaging framework - Email Advertising platform and APIs for multichannel display ad campaigns - DSP / CDP design, architecture & integrations

Acquired by SendGrid. A product studio for developer tools/services.

RatePoint, founded with other former GeoTrust co-founders to help small businesses collect, manage and promote consumer driven reviews & feedback. Operators of local business email and survey platforms to support local business growth Designed and operated reputation api/knowledge graph for local businesses Designed & Powered API first likeness & recommendation engine for SaaS integration

Acquired by VeriSign/Symantec (2006) Digital Certificate Provider (SSL, TLS, S/MIME) Inventor of domain validated SSL certificates. Committee of EV SSL Standards Builder & operators of Anti-Phishing API’s and Services Platform (major browsers integrated) Operators of ubiquitous Certificate Authority platform Operators of managed PKI, S/MIME services for fortune 100 companies

Acquired by GeoTrust Managed PKI / Digital Certificate & Signing Platform Software Code Signing Services Platform First ubiquitous Certificate Authority platform VPN & S/MIME management platform (Secure Email) Digital Certificate Provider (SSL, TLS, S/MIME)

Internet Service Provider (ISP) - Operated from 1.5 POP (others had ~6) - Local dialup & business connections - Frame relay and network mgmt for State - DNS management services for large cos and providers Competed with AOL @ 25/mo for unlimited Web & Application Development Infrastructure design and build out (telco pots through digital)

Designed & built (engineered & product) data collection, monitoring, and reporting infrastructure for ISO standard / compliance.