Talking near monkhood, the Midwest & the Wild West of private market investing

Key Takeaways:

  1. Don’t follow in anybody’s footsteps. Build a thesis and venture capital firm that is authentic to you, your passions, and your experience, not just what you see in the market
  2. As a VC fund manager, provide a key value add for your portfolio companies. Push your founders to grow outside their comfort zone as a mission-aligned partner for your investments as opposed to just a fund manager or venture capitalist.
  3. When building a 506(c) or rolling fund, use your network and connections to publicly advertise to potential LP investors. …

Talking secret clearance, Twitter, and diamonds in the rough

Mac Conwell of RareBreed Ventures
Mac Conwell of RareBreed Ventures

I had the pleasure of meeting Mac through Twitter then over Zoom last October. Over the holidays, I sat down with Mac Conwell to chat about his journey as an emerging manager, launching RareBreed VC, his investment philosophy, and his advice for those who want to follow in his footsteps.

McKeever “Mac” Conwell II is a software engineer by trade and was a former DOD contractor with “top-secret clearance doing a lot of cool stuff I can never talk about.” Mac spoke candidly about the highs and lows of his early career that ultimately led him to VC. He was…

Part 4: Managing Your First Fund as a Business and Building Fund II, III and Beyond


  1. 95% of VC funds fail. In addition to your passion and commitment, bring operational experience to juggle investing, fundraising, and running your small business.
  2. In the VC model, labor is a scarce resource. If you build a larger Fund II or III, consider the toll a higher volume of deals will take on your labor force.
  3. Most VC funds are under-diversified. You’re going to learn as you invest and the world will evolve as well — give yourself enough flexibility to readjust, adapt, and take advantage of the opportunities that come your way.
  4. When you’re in Fund I, you’re…

A Guide For Emerging Managers

Part 3 of 4: Pursuing Leads & Getting to Yes


  1. Tap into your 1st, 2nd, and 3rd degree network to cast a wide net when looking for potential investors to build support before your search becomes more targeted.
  2. Set deadlines and create a sense of urgency to quickly build momentum and get LP commitments.
  3. Communication is key when fundraising and managing your fund. Even if a lead goes cold, foster that relationship and stay in contact.

Once you’ve laid the groundwork for your first fund — building your network, identifying your secret sauce and motivation, developing your thesis, and modeling your fund — how do you move forward?


A Guide for Emerging Managers

Part 2: Fund, Thesis & Pitch Deck


  1. There are about 900 micro VCs in the market representing demand for ~$20 billion in capital commitments every 2–3 years. Set yourself apart with 1) thesis-driven conviction and alignment 2) differentiated deal flow and access to founder communities, and 3) added value beyond the check.
  2. Right now, over 358 emerging and micro-VC managers are actively raising a new fund. Craft your thesis and fund from your passions and experiences to handhold LPs down the path you’ve walked that proves you have a unique position or lens to evaluate and invest in talent.
  3. Micro VCs raise anywhere up to $100M…

A guide for emerging managers

Part 1: Ecosystem, Network & Team


  1. Leverage your reputation and network to show early investors that you know enough people in the industry and have access to strong, proprietary deal flow.
  2. Show any traction including previous investments or high-quality deals you scouted or helped investors close. Track key metrics and convert them into pitch decks.
  3. Anchor your commitment to raising your first fund with a clear personal motivation. Why you want to raise a fund will help explain why you are the right person to raise a fund.
  4. Surround yourself with great people building great things.

How to manage up from the top rung

Photo by Mael BALLAND on Unsplash

Take action now:

  1. Figure out what makes your team tick and what you can do to empower them to succeed. Both personally and professionally.
  2. Share control and authority, and delegate responsibilities.
  3. Focus on every situation as abundant. Fuel your Smart Creatives, share ideas and connect with your team members on a personal level to help them grow and find success.
  4. Harness the passion of your people and give them the tools to put their skills into action.
  5. Get out of the way to allow your team to perform.

Managing up is a skill generally used by middle managers to guide…

What’s important in finding success? And what isn’t?

Key Points:

  1. As a leader: be tenacious, be coachable, and have integrity, above all else
  2. As a team member: build partnerships and relationships
  3. As an entrepreneur: ask questions, foster the right ideas, and convey your passion

The story of the young upstart founder is a popular narrative in today’s culture, but how genuine is it? A recent article by Ian Hathaway actually reveals that, on average, the most successful founders are in their 40’s. …

A quantitative portfolio management system for investors

What problem are we trying to solve? How did I build fiifi? How can you get your free account?

For several years I was frustrated that I couldn’t find a portfolio management tool to serve my needs as an investor. I started asking my colleagues if they had the same problems as I did regarding deal flow, system of record, and data aggregation with early stage investments.

I began with user interviews to refine my hypotheses about what investors want and need in portfolio analysis. After this validation, I started building and testing against those same people who would be my customers. Step by step, this became fiifi.

Having the right idea is an evolution of product, user interviews…

What a VC is thinking, How did we get here, Where’s my inspiration

Photo by Kimberly Farmer on Unsplash

Every morning from about 5–7 AM, I block off my schedule to read; anything from business news and books on entrepreneurship and VC to sci-fi and biographies. I usually have about 5 books on rotation, currently including these 3.

I usually try and read books I can burn through at a decent pace. As I have a little bit more time now without travel, meetings and events I have added some longer form books to my reading.

Surprisingly, these three books have helped me better understand the…

Theron McCollough

The Founder VC; founder/CEO at; past Managing Director @SVB_Financial #startups, Investor at Acceleprise

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