Be the Tortoise not the Hare

May 14, 2025

Learn why cross-sell is your new best friend :)

Cross sell- be the tortoise not the hare!

In my last blog I wrote about how for a bootstrapper driving a best in class customer experience is more important than winning new logos and chasing new business. This naturally leads into a focus on developing new adjacent products with these same customers and cross selling to them. Investors will want you to grow by diversifying your client base, expanding your footprint and winning new logos. In doing so they argue that you will reduce concentration risk and start driving scale. You need to do the opposite.You want your initial customers to be from the small end of town especially in b2b. Unlike with the larger players this means you will be able to get direct feedback on your product as you iterate to build product market fit. Once you have that you need to keep your focus on this same group of small players.  Why?

This is because this is where your low cost risk reduced product growth and new revenue generation is going to come from. You have a product market fit and you are using your meagre bootstrap funds to drive growth. The point at which you can no longer take on any more new customers without needing to expand your human resources to service them,  is the point in time when you double down on your focus on your existing customers.

You are now fundamentally in a different position to when you started. At that point you didn’t have a product, relationships or any kind of brand recognition from your potential customers. That has now all changed.

You have worked with them to iterate and refine your product to achieve product market fit. By doing so you have both onboarded them as paying customers, built close relationships with them and importantly solved a pain point for them. You have also hopefully delivered an outstanding UX. You  are no longer thew new kid on the block but you are now a trusted and proven partner.

You are ‘inside the tent.’

This is where you want to be. It is practically unheard of for a customer to only have one pain point that needs solving.  As a new supplier outside the tent you have identified their no 1 pain point and solved it for them. You have also done this for a number of small but similar clients as part of achieving product market fit. Now you are in the tent it is the time to leverage your position. As a proven and trusted partner who solves problems you can use your relationship to start to identify other pain points they have that need solving.

When you were outside the tent and an unproven partner your client may have been reluctant to share these with you. Now that the situation has changed you will be able to work with them to identify these. On top of that your client base all have a similar DNA  and it is therefore likely that the pain point that one has is similar for all your other clients. Now is the time to create adjacent products and to cross sell.

 There are some big advantages for a bootstrapper to this approach. As a bootstrapped founder you need to be constantly focused  on two key goals – reducing risk and maximising cash. You need to do this while making sure your base is sustainable and that you are continuing to grow. In order to grow your business sustainably in as risk free and capital restraining way as possible, building adjacent products and cross selling them to your existing base is the way forward. Cross-sell is your friend.

 By focusing on the new pain points of your existing customers you usually end up with a product that is a variant or alternative to your existing initial product. This is your specialist area of knowledge, skills and competencies. This means that you can identify, build it and start selling the new adjacent product with minimum capital outlay and without increasing human resources. By using this method you can optimise both your human and capital resources while minimising the risk. You don’t need to pay for extra product people or software, new business people or even CX people. By both developing it with and selling it to your existing customers you are working with clients with who you already have a relationship and in doing so, further deepening that relationship, increasing your chances of success and revenue generation while at the same time reducing your business risk.

 For a bootstrapper this is a safe and sustainable way to achieve fast growth. The only potential negative is your concentration risk as you now have more revenue with the same number of clients. This is partially true but at the same time you are deepening your relationships with these clients so I would argue that you are also effectively further protecting those initial revenue streams and actually reducing the overall business risk.

 The alternative growth method of winning a huge number of new logos is fraught with cashflow and reputational risk as I discussed Don’t chase new business! | LinkedIn . Developing new product lines with a different set of customers is also fraught with both capital and human risk. Working with your small existing customer base to develop adjacent products and cross- selling to them to generate new revenues allows you to grow while reducing your capital and financial risk.

Investors would want you to be the hare. Be the tortoise.