1. Reputation is how you’ll get started: Having advocates to help you win business based on your reputation early on can be a big lift, but it won’t take you all the way. Understanding the persona you’re selling to and how to speak their language is also critical.
2. Build specialist teams to target new personas that your core team cannot reach: Your team will do their best, but solution sales will be necessary for the first push. This is especially true before you specialize your sales team by customer type. 
3. You’ll have to simultaneously push your core product and your new products: If your sales team neglects the core product in favor of the new product, your revenue might suffer while the new product gets started. Finding a balance is crucial to creating excitement about new products and keeping your sales team meeting quotas. Look for adjacencies where a new product will make an easy cross-sell.
4. Keep sales teams focused with guardrails: The temptation with new launches is to go too cheap or too wide. ServiceNow avoided this trap by setting a minimum contract value with pricing floors.
5. Don’t over/under-index too quickly: These things take time beyond the one or two quarters that Wall Street will push you to have. Gather as much data as you can in order to learn what’s working over the long term. As Kevin says, “It’s not just about whether we could build this great product. Should we build this great product?”

We hope you enjoy this interview with Kevin.

1. The starting position is perhaps the most important
2. Everyone needs an Eric Hemmer to help the customers: Eric was a scrappy generalist who was willing to lead customers to the next level. You need to make sure you have the right people as you start to expand, as they will set the DNA of the organization. If your employees believe you can be a platform, your customers will too.
3. Follow a maturity model as customers grow
4. Building platforms is about balancing trade-offs
5. Focus on creating the best experience, not just being first

Esben shares the differences between his previous venture-backed company and Userflow's bootstrap mentality. He also discusses Userflow's ambitions, which center on continuing to build a great product and business rather than pursuing an exit. For any software founder considering bootstrapping, this interview offers an inside look at how Userflow has made it work.

We hope you enjoy this conversation with a new bootstrapped legend. 

The belief in his team and in his company also started with a belief in himself. He acquired Merkle when he was 24 years old for $5.3M. To save money while he was raising the money to buy out the company, he moved his family into his grandmother’s house in a retirement community for almost an entire year. From there, he bootstrapped the company for another 20 years before raising outside capital. 

Ultimately David and Merkle’s story is about the power of compounding. What happens when you consistently, constantly, relentlessly give your best to a company for multiple decades? The answer is simple: magic happens.

We cover some of the many ways CargoWise broke the mold:

• Their sales staff are not allowed to do demos of the software
• Customers cannot email or call when they have a problem with the software
• No secret discounts are allowed, ever.  All prices are public and updated every month.
• A strong point of view on how work gets done—so much so that the company fields a Wisetech Academy and builds almost all operating systems and software in-house, including a task management system that manages every employee’s work product systems

We hope you enjoy this expansive interview with CargoWise co-founder and Tidemark Bootstrapped Legend Richard White. 

If you’re interested in staying in the loop when new episodes of Bootstrapped Legends launch, you can subscribe 

here. 

If you're a Bootstrapped Legend who wants to tell your story or learn more about working with us, please reach out to us at 

knowledge@tidemarkcap.com. 

One of the largest benefits of bootstrapping is the independence it grants—throughout our conversation, Jason continually brings up that benefit. In their business, they actively avoid enterprise customers and focus on serving small businesses. Instead of setting goals, the company focuses on a repeatable product process. Rather than be driven by a board’s demands for unrelenting growth, they are driven by the passion for what they build.

Even their marketing is different—they open-source their ideas through books to spread their philosophies and gain influence. They only recently began experimenting with paid marketing (can you imagine not doing that for 25 years??), and everything they make has a deliberate, handcrafted feel. 

At Tidemark, we love these types of entrepreneurs. Their stories and strategies are worth studying. We hope you enjoy this conversation with Jason Fried.

• Almost everybody who was in a senior management position by the end was somebody hired directly out of college
• Implementing “unscalable” sales strategies like making a custom website for each customer so all they had to do to get started was say “yes”
• Taking a 6% transaction fee versus the per-seat pricing of their peers
• Doing full-cycle sales where one rep owns an account from start to finish—no SDRs or blanket cold call campaigns

Their unique approach of providing turnkey software, onboarding, and pricing separated them from competitors and helped them land and grow accounts rapidly. Despite running on a shoestring budget for years, Lawrence attributes FareHarbor's success to a “GSD” culture and the hustle of their scrappy early team. 

We hope you enjoy our conversation with Bootstrapped Legend (and Tidemark Fellow) Lawrence Hester. If you’re interested in staying in the loop when new episodes of Bootstrapped Legends launch, you can subscribe here. 

If you're a Bootstrapped Legend who wants to tell your story or learn more about working with us, please reach out to us at knowledge@tidemarkcap.com. 

ExactTarget was my first lead investment at my previous firm, and I was fortunate to sit on Scott’s board as we accelerated aggressively through the 2009 global financial crisis. We ultimately took ExactTarget public—the biggest SaaS IPO then—and later sold it to Salesforce.com in the largest acquisition they had made up to that point. Over that period, we scaled to close to half a billion in ARR, and we’ve heard that ExactTarget is still growing strong, reaching $2B+ ARR inside of Salesforce. 

As I look back, I'm not sure if I realized at the time quite how remarkable what we did with ExactTarget was—both the decision to forward-invest in growth while the sky was falling and the precise execution of the team. Two and a half recessions later, the story stands out to me even more.

We hope you enjoy this conversation with Scott as much as I did.

About Tidemark

Tidemark is a venture capital firm, foundation, and community built to serve category-leading technology companies as they scale.  Tidemark was founded in 2021 by David Yuan, who has been investing, advising, and building technology companies for over 20 years.  Learn more at www.tidemarkcap.com.

• Knowing when you’ve hit a wall (in this case, TAM)
  • Knowing when you’re reaching saturation vs. execution
  • Real functional TAM vs. the slideware construct
• The importance of finding a new leg of group before core slows down
  • Managing your product portfolio to get your core to profitability in order to fund new s-curves of growth 
• How to get profitable and where to look for operating leverage
• Moving from venture capital investors to private equity

As an entrepreneur, you hit roadblocks, and one of your superpowers is finding crafty ways around and/or brute-force ways through. But sometimes that is not the right approach. After running into a roadblock many times, it might be time to pause, cut back, and get your economics in order to create time to build a strong fundamental business, and then reaccelerate growth. 

I hope you enjoy this conversation with Nick Mehta about “slowing down to speed up” to create a strong fundamental business. 

About Tidemark

Tidemark is a venture capital firm, foundation, and community built to serve category-leading technology companies as they scale.  Tidemark was founded in 2021 by David Yuan, who has been investing, advising, and building technology companies for over 20 years.  Learn more at www.tidemarkcap.com.