Michael Woolf

Decision Strategist who helps servant-leaders, visionary founders, and wicked-smart operators reimagine boundaries, achieve the impossible, and build people-first cultures

Nashville, Tennessee, United States

About

The biggest mistake leaders make when scaling a company has nothing to do with their strategy, their tech, their product, or their talent… If you look carefully, you’ll notice they share one thing in common that most leaders never talk about: They’re led by people who see the whole system, not just the parts. Treat culture, operations, and legal as separate worlds, and friction multiplies. Decisions get slower. Risk increases. People disengage. And eventually... growth stalls. Culture, operations, and legal can’t be separated. They are a system. Integrate them well, and you, too, will scale your business while maintaining its soul. --- Here’s what I’ve learned helping founders, CEOs, enterprise leaders, and boards navigate complexity: 1️⃣ Vision without safety collapses. Work only transforms into play in environments where people of principle unite, tell the truth, and trust each other enough to experiment to create great products and services. 2️⃣ Curiosity beats control. The companies that scale are the ones that encourage questions, not perfection. Ones where accountability thrives when curiosity is nurtured. Where mistakes are never a cause for termination. 3️⃣ Values only matter if you practice them daily. Here are the ones I live by and teach: • Do the right thing, especially when no one is watching. • Tell the truth, even when it’s hard to hear. • When you eff it up, own it and work like hell to make it right. • Value relationships over dollars and people over profit. • Take criticism seriously, not personally. • Celebrate failures as well as successes, and learn exponentially faster. • Show up ready to roll up your sleeves and play. --- For nearly 30 years, I’ve stood at the intersection of business, technology, strategy, and law. I've developed expertise in software development, entrepreneurship, business/SMB, leadership, technology, operations, IP, and law. In that time, I’ve seen a striking pattern emerge: True leaders are master players in an infinite game. These leaders build lasting environments where people grow, decisions align, and risk becomes manageable instead of paralyzing. I've learned that if you want to build a company that grows sustainably while being a joy to lead, you'll need to find a strategic partner who will encourage you to think broadly, solve deeply, and lead with clarity. If you think I might be that fit, I'd love to hear how I can help: https://www.boonlegal.com/meetwithmichael/

Experience

  • founder and legal advisor at Boon Legal LLC
    2018 - Present · 8 yrs 7 mos

    Boon Legal is a business law firm built by entrepreneurs for entrepreneurs. • Built a law firm of entrepreneurs for entrepreneurs by leveraging a gap in the legal industry: lack of affordable legal services for the startup that need it the most in their early years. Profitable since inception with an average 183% annual growth. • Introduced subscription-based and flat-fee legal services to remove barriers to client communication; adopted virtual, paperless office strategy to reduce overhead; leveraged prior business and technology experience to improve efficiency; and focused on making quality, budgetable legal support available to clients when and where they need it. • Build relationships with clients, as member of their executive teams, while advising on strategies and goals to address business challenges and proactively mitigate risks and potential issues. • Research, write, and speak publicly on issues affecting rapid growth of startups and small- and medium-sized businesses and the intentional crafting of culture in companies.

  • council member at GLG
    Mar 2021 - Present · 5 yrs 5 mos

    GLG is a global knowledge marketplace trusted by leading decision makers. It connects thousands of clients who want the advantage of powerful insight to the largest global network of subject-matter experts across every sector.

  • founder at Boon Partners
    2017 - Present · 9 yrs 7 mos

    Boon Partners was conceived to help entrepreneurs and small- and medium-sized businesses to succeed in an ever-changing environment. We consult with and coach entrepreneurs and small- and medium-sized business operators so they can become more effective, people-first leaders in order to create cultures of growth and empowerment in their organizations. Only by putting people first can an organization truly become empowered to solve its toughest problems and reach its greatest potential. Boon Partners helps leaders learn how to: - create and communicate a shared vision - create a culture of empowerment and growth for all stakeholders - own the reality of the actual while aspiring towards the (not yet) possible - develop a learn-it-all mentality and growth mindset to help iterate, validate, and repeat - focus on building value internally so the members of the organization can focus on building value externally - plan for the future while remaining agile and nimble in the present

  • attorney at Baker Donelson
    2016 - 2018 · 2 yrs

    • Recruited by AmLaw 100 firm to serve clients in the areas of emerging companies, software and technology, data privacy and security, and protection of intellectual property. • Conducted research and was consulted as in-house subject matter expertise in the legal aspects of artificial intelligence/machine learning and open source software technology licensing; authored and published multiple memoranda and articles on these and other key technology issues as they pertain to the law. • Drafted documents for business planning and formation, capital raises, and mergers and acquisitions. • Performed due diligence analysis for M&A deals and other business diligence matters. • Researched and drafted (1) privacy policies and procedures for businesses, web-based and standalone applications, and cybersecurity and data compliance services; (2) vendor- and customer-friendly software licensing and development agreements; and software/technology license and terms of service agreements. • Led a team to evaluate new software tools for firm-wide adoption and the marketing of those tools to existing and prospective clients.

  • director of product development at DevDigital
    2012 - 2016 · 4 yrs

    • Grew a 3-year old dev shop from 8 to 27 persons in the Nashville-based project management and sales division, and, in the off-shore development division, from 37 to 154 persons while managing multiple concurrent production teams. • Created a PMO to institute PM best-practice processes and standards for software development teams, utilizing a hybrid PM process which merges agile, waterfall/CPM, and kanban methodologies to drive improvements which resulted in an average of 183% in annual revenue growth. • Led the development of a proprietary project management software (combining time and task tracking with resource allocation capability via a team hub and integrated CRM) that resulted in a 135% increase in dev team efficiency and increased sales by 167% in the first six months following roll-out. • Spearheaded a special project aimed at positioning company to acquire equity in various companies and helped to build a subsidiary holding company for equity projects and internal IP. • Designed, architected, and planned product cycle product cycle from concept-to-launch for largest project in company history – a $1.5M LMS platform designed to deliver DRM content to 22,000+ college students in the California State prison system via air-gapped custom tablets – which was delivered early and under-budget. Awarded 2015 Outstanding Project Team, CDCR, State of California. • Articulated project goals and scope; translated business needs into technical requirements; negotiated and prepared detailed work breakdown structures (WBS); and instilled a culture of shared accountability to achieve on-time/under-budget project completion. • Worked hands on training and mentoring emergent dev team leaders to develop their skills in analyzing, detailing, planning, architecting, and managing multiple, concurrent product lines and projects.