From Slow Starts to Successful Demos: The Power of Cold Email Outreach

Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app. Today we're going to dive into the stress that comes with entrepreneurship and how it shows up in their personal lives. Moving up from one customer segment to another is hard. Each customer segment is like an Island with a body of water between them. They're crossing that body of water from servicing one and two-person teams to serving larger architecture firms with 20 person teams. We hear how they are managing this difficult and stressful moment both as co-founders and as married partners.

The topics we cover

[01:40] Leveraging testimonials when moving upmarket

• It's an approach you should explore as early as possible when trying to move into a new segment of the market
• One of the reasons why trials are kind of a little bit lower this month is because some of the traffic that we've been getting is probably more geared towards the residential side and they're seeing this new messaging.
• You have two islands and a body of water in between them and its messaging and sales process and pricing and positioning and all that around going after one person, two-person teams versus a 10 person team and those are the two different islands.

[06:09] Cold email experiments to attract larger teams

• Averaging 12-15 demos per week (initial goal was to get to 10)
• Finding one repeatable channel at this stage is huge
• Cold email has been the channel that has worked the best for Brian & Scottie
• Most businesses that start B2C end up transitioning to B2B and end up raising prices. Means less churn, fewer flakes for demos, better conversion.'
• Demo to trial isn't as high as they'd like it to be.
• One reason for this could be due to the longer sales process

[11:27] Cashflow management

• We had a really good month last month -- the best month we've ever had.
• The biggest stress is just around the channels that we're investing in and wondering if they are going to perform like we want them to.
• These are challenges with going upmarket. First, you have to figure out if you have product-market fit with teams. Then you have to find a channel or two that work. If the channel works, do the people stick around and can you find enough people who sign up and stick around? Can you find them fast enough with the channels you have such that you don't run out of cash
• At the current burn rate we have about 6 months cash in the bank
• If pushed, would consider debt-equity or debt financing as a fallback option
• Founders do all sorts of things to maintain their runway, including credit card debt, personal loans, raising funding, even borrowing from their 401k. But with each of these, you have to weigh the risks to the business, as well as your personal financial situation.

[18:09] Dealing with stress as entrepreneurs and a married couple

• The situation causes us to feel a little bit on edge and we have no one else to take it out on.
• Now we're being much more conscious of our personal spending ad so I think that has also manifested itself just a little bit in some additional stress because we're really tracking all of our expenses really tightly and we're making sure that we don't spend foolishly.
• No silver bullet for stress, but certainly meditation, exercise, and being aware that you are stressed.
• Even though there is this sort of stress and there's sort of some existential risks to this experiment that we're running, it also feels aligned with where we want to go as a family and as an exit plan from work life at some point.

Links from the show

• Default Alive
• Equity Financing vs. Debt Financing: What's the difference?
• Gather | Website
• Brian Elliott | Twitter

Thanks for listening to another episode of TinySeed Tales. If you haven't already, be sure to check out Season 1 of TinySeed Tales where we follow the Saas journey with Craig Hewitt of Castos.