"When to cross (or burn) a bridge"

Happy Friday Doriot Community!

High five to the 3 new members this week! ✋ 

🤓 Official Pronunciation of Doriot: dor-ee-oh (What’s up with the name?)

Our Pitch: Venture, unlocked for the ambitious yet underserved

We’re aiming to build a unified community of underserved founders and investors to drive elite-level venture returns through the emerging retail venture pathway.

Unlike traditional venture, which is built for existing wealth and exclusive networks (the overserved), we’re creating a venture community of smart and ambitious outsiders (the underserved), focused on generating new wealth and networks.

By teaching Georges Doriot’s proven, disciplined model of venture alchemy and uniting thousands of small, committed venture investors into a new force in venture, we believe we can outcompete the privileged—not on status, but on wins.

Thus, each week, we intend to explore a component of Venture Alchemy, applicable to many areas of life, along with key lessons on the business of venture as the foundation upon which a new venture system might emerge.

If this approach resonates, welcome—there’s much more to come! And if you think others would benefit from this journey, please forward our newsletter!

Doriot Moderating Wefunder Pitch Event!

Next Tuesday (9/24, 2:00-3:00PM ET), Doriot Founder & CEO Gerry Hays will be moderating and questioning a panel of three startup founders currently raising a community round on Wefunder! We’d love to see strong representation from the Doriot Community. Click here to register!

Venture Alchemy - This Week’s Discussion

“One if the hardest things in life to learn are which bridges to cross and which bridges to burn.”

Oprah Winfrey’s quote, "One of the hardest things in life to learn are which bridges to cross and which bridges to burn," highlights the importance of knowing when to pursue an opportunity and when to let go.

Whether it’s a relationship, a job, or a habit, one of the hardest decisions is knowing when to say 'no' or move on from something you’ve previously committed to (burning a bridge). Your ability to make these choices sharpens the more you understand who you are and where you want to go (i.e., your vision). If you’ve committed to a vision but continue engaging in something that doesn’t align with it, you’re wasting time, energy, and resources—risking a cycle of negative emotions like guilt, shame, or regret, which can create a damaging feedback loop.

This wisdom is especially relevant to startups, where tough decisions are a daily reality. Founders inevitably face make-or-break moments, particularly in the early years, and must determine which opportunities to pursue and which to set aside.

Thus, focus is key. Knowing when to lean into opportunities, habits or relationships, or to cut ties with initiatives, habits or relationships that aren't contributing to the startup’s growth, is critical to staying agile and competitive over time.

Applying the Venture Alchemy Formula to Oprah’s quote:

• Mindset: Be clear on the goal you want to achieve and, most importantly, why you’ve set out to achieve this goal. While your tactics and strategies may evolve, your "why" should remain constant—it sustains you.

• Strategy: After you've clearly defined your goal, identify specific, actionable steps that align with it. One common mistake is trying to tackle large goals all at once. To be more effective, break down your main objective into smaller, manageable tasks or milestones. This not only helps keep you organized but also allows you to adjust your strategy as you achieve each milestone.

• Execution: Put your plan into action, testing and learning along the way. Stay focused on what’s working and be ready to adjust if needed. The goal is to keep refining your path to ensure it’s bringing you closer to your objective. But give yourself grace—much of what you try won’t bear fruit immediately. We can easily overwhelm ourselves, and that’s when we’re most susceptible to losing focus.

  And, for those who struggle with staying disciplined, consider reading First Things First by the late Stephen Covey. He teaches how to prioritize tasks into four categories: 1) Important and Urgent, 2) Important but not Urgent, 3) Urgent but not Important, and 4) Not Urgent and not Important.

  

Venture Lesson: The Power of Free

By: Gerry Hays

Last week, we discussed recurring revenue models. This week, we’re going to focus on the power of free when as part of the revenue generation process.

From Low Prices to Innovation

Back in 2008, I was approached by two former students to buy into their startup, a custom t-shirt business specifically catered towards Greek life and events (e.g., barn dances, homecomings, etc.). Their pitch was that they had devised a system to win orders over the competition in what is a low barrier to entry business. Fast forward a few months as we tried to expand into multiple universities, and we discovered that, without a strong relationship, the 'lowest price' always won the deal. This happened repeatedly, and despite excellent execution, there were customer behavioral challenges that were hard to overcome. I began to resign myself to the fact that this wasn’t going to be a winner.

Then, my favorite magazine, Wired, arrived in the mail (yes, getting magazines delivered to a mailbox used to happen). In this particular issue, Chris Anderson’s book Free (he was the editor of Wired) was being released and they featured a lengthy excerpt of the book as the main article.

Anderson was arguing that there has never been a more competitive market than the Internet, and every day the marginal cost of digital information gets closer to zero. As a result, two trends have driven the spread of free business models across the economy, a reality that holds true today. The first is the classic "give away the razor, sell the blades" cross-subsidy model. For example, OpenAI offers a free version of its LMS for everyone, but if you want a more robust version, you're paying a monthly fee. Similarly, Dropbox provides free, limited storage, but for more space, you pay a subscription. The second trend is the digitization of businesses. One example is Google transforming advertising (once an expensive business) into a software-based, much cheaper model. This approach has since been applied to industries like banking (e.g., Chime) and gambling (e.g., DraftKings), among others.

And from the consumer’s perspective, there is a huge difference between "cheap" and "free." According to Anderson, give a product away, and it can go viral. Charge a single cent for it, and you’re in an entirely different business—one of clawing and scratching for every customer. This is referred to as the “penny gap.” It reminded of when the Internet first started, and a company called Prodigy was by far the market leader in bringing people online in 1993. They discovered that their email feature was wildly popular but expensive to maintain. So, they created a policy allowing 30 free emails, and then charged $0.25 per email thereafter. This led to tens of thousands of members leaving the service, eventually causing them to lose massive market share to AOL, which offered free messaging. A different decade in terms of technological advancement, for sure, but consumer psychology remains the same today as it did in 1993: Free wins.

With this in mind, I challenged the team to think about how we could make T-shirts free for our target audience. Since T-shirts are analog, there’s a real cost for materials, printing, shipping, handling, etc. While we couldn’t turn a T-shirt into software, we could consider a cross-subsidy model—giving away the shirts and having advertisers who wanted to reach this specific demographic cover the cost, plus a profit for us. We then filed (and were subsequently issued) a patent for the business model. From there, we raised two rounds of capital to prove out the concept and were eventually acquired by Custom Ink. In essence, we went from competing in a hyper-competitive market to being in a space with no competitors—no other custom apparel company was offering free T-shirts.

Thus, every startup needs to consider applying the model of 'free' to their business, and it doesn’t have to be as dramatic as securing a patent. Here are five quick strategies to offer your targeted customers for free:

1. Market Research Reports: Provide free, concise reports on current market trends, consumer behavior, or industry forecasts to help your customers stay informed and competitive.

2. "How-To" Content: Create specific, actionable guides (e.g., "How to Boost Customer Retention" or "Optimizing Digital Marketing for Small Businesses") that offer practical solutions to common challenges.

3. Free Consultations or Audits: Offer free 15-30 minute consultations or audits of their business processes, digital presence, or marketing strategy, giving personalized tips for improvement.

4. Expert Interviews or Podcasts: Host interviews or podcasts with industry leaders and thought experts discussing relevant topics that provide valuable insights for your audience.

5. Resource Library: Build a repository of free tools, templates, and checklists (e.g., project management templates, business development checklists, or digital marketing calendars) to help them streamline their operations.

Next week, we’ll dive into Trademarks and URLs and their importance for startups.

Next Week’s Diligence Report

For Premium Community Members, we’re going to analyze Fierce Foundry, currently raising on Wefunder. 

Have a great weekend, everyone! We’d be grateful if you could forward this newsletter to anyone in your network and invite them to join the Doriot Community!

Sincerely, Team Doriot!