When you’ve made all the startup sacrifices, and it’s not enough — Dave Boyce on resilience
When you’ve made all the startup sacrifices, and it’s not enough — Dave Boyce on resilience
How a GTM-focused SaaS Advisor and Board Member turned huge challenges into motivation for a successful journey from entrepreneur to professor and PLG author.
Hey it’s Andrew.
I’m currently on a plane to Florida to spend the week enjoying some sunshine and hanging with my 95 yr old grandfather! I’m normally not a laptop on the plane guy, but with a 3 yr old (and another on the way) I’m sneaking in a few extra mins of work.
I’m excited to share 3 things with you 👇
Below, you’ll hear about the 3 toughest moments in Dave Boyce’s career - and how he navigated them.
You can now enjoy clips from the show on Instagram and TikTik.
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“Hey Dave, this is going to be a tough conversation. Do you have a minute?”
Dave Boyce was cruising down the El Camino Real when the call came in.
It was George Zachary — the renowned investor who made his name by investing in Twitter. George had made a seed investment in Fundly — the company Dave was working on. That investment had brought in others, helping the startup raise $2M to get up and running.
George said he was pulling out of Fundly – a huge blow.
“We had sold our dream house in Boston and moved our family (with six kids) to Silicon Valley,” says Dave. “We self-funded for a year. My kids’ college funds were gone — invested. We were renting instead of buying. We’d hired eight or ten people whom I loved. I cried a lot.”
Dave was 0 for 39 on pitching the business. And Zachary was out, which would send a not-so-great market signal. Things were bleak.
Zachary’s advice: “This is going to be really tough. I don’t know how you’ll get through it, but you’ll figure it out. Your toughest enemy will be in the mirror. Don’t let yourself get down.”
Dave did stick it out, and that 40th pitch landed a $5M round — sending Fundly off to the races.
We talked about this story and other speed bumps on Dave’s journey to becoming a serial entrepreneur who evolved into a professor and a writer, and who is on the boards of Winning by Design and Forrester.
Highlights include:
The time Dave moved his family to South Africa in pursuit of a healthy bonus and leg up, and instead got some of the toughest feedback of his career
The other time Dave got really bad news (his job was being eliminated), and how he avoided overreacting and instead looked for alternate solutions
How he battled imposter syndrome to create a consulting business, put together a college course, and start writing a book on PLG.
Watch or listen below 👇
Specific moments to listen for:
[04:52] What happened when Dave ignored his gut feelings
[12:26] Dave’s spontaneous decision to move to South Africa with his family and ended up receiving the toughest feedback in his career
[26:13] Receiving a call from George Zachary (CRV), saying "This is going to be a tough call. Do you have a minute?”
[32:53] The moment Dave experienced imposter syndrome and almost threw the towel in.
[36:50] Dave’s secrets behind what helped him pursue his dreams
Resources:
Connect with Dave on LinkedIn
Subscribe to Dave’s Substack
Subscribe to the Delivering Value Substack
Learn more about Navattic
Learn more about Appcues
Interested in sponsoring the pod? Let’s chat! sponsor@deliveringvalue.co