What if your startup does not have a product problem, but a pricing, positioning, or customer problem?
In this episode of Executive Connect, Melissa Aarskaug sits down with Alex Shartsis, founder and CEO of Skip and Silverwood, to discuss why so many founders undercharge, chase the wrong customers, and mistake activity for real go-to-market traction.
Alex explains why charging early gives founders better feedback than free users, how highly targeted micro campaigns can outperform mass outreach, and why narrowing your ideal customer profile can make both product and marketing more effective. He also shares how founders should think about venture capital, bad-fit customers, scarcity thinking, and knowing when a business or strategy simply is not working.
The conversation also covers value-based pricing, fair packaging, AI-powered go-to-market, customer conversations, and why founders often abandon a working channel too quickly in search of the next opportunity.
For founders dealing with inconsistent revenue, the message is simple: get closer to the customer, understand where value is created, and stop changing direction before you have enough data to know what actually works.
What You Will Learn
- Why founders often undercharge for what they build
- How charging early reveals whether real demand exists
- Why the wrong customer can look like a pricing or product problem
- How micro campaigns can outperform mass outreach
- Why narrowing your ICP makes messaging and product decisions stronger
- What founders should understand before raising venture capital
- How scarcity thinking can lead to bad customers and bad decisions
- Why perceived fairness matters in pricing and packaging
- How AI is changing go-to-market execution and team responsibility
- Why founders should improve a channel before abandoning it
Chapters
(0:25) Why startups struggle with pricing and go-to-market
(1:31) Why founders consistently undercharge
(3:42) Pricing problem, product problem, or wrong customer?
(7:37) Why micro campaigns outperform mass outreach
(13:10) The power of narrowing your customer niche
(17:06) The hidden traps of venture capital
(19:23) How scarcity thinking hurts founders
(26:44) Building fair, value-driven pricing
(34:05) How AI is changing go-to-market
(42:53) What founders should do when sales stall
**Alex Shartsis** is the founder and CEO of Skip and Silverwood, where he works on pricing, packaging, customer acquisition, and go-to-market strategy. In the episode, he shares experience across bootstrapping, venture-backed companies, acquisitions, exits, and shutting down businesses, giving him a broad view of what actually drives sustainable startup growth.
His approach emphasizes disciplined pricing, tightly defined customer segments, thoughtful outreach, and validating demand through real purchasing behavior rather than vanity metrics. He advocates charging early, focusing on customers with meaningful pain, and building sales and marketing around measurable value.
Alex also brings a practical perspective on venture capital, AI, and founder decision-making. Rather than chasing growth at any cost, he encourages founders to understand their economics, choose customers intentionally, give experiments enough time to work, and stay close to what the market is actually telling them.
**CONNECT with Alex Shartsis**
Website: https://skyp.ai/
https://silverwood.ai/
LinkedIn: https://www.linkedin.com/in/shartsis/
CONNECT with Executive Connect
Website: https://www.executiveconnectexperience.com/
LinkedIn: https://www.linkedin.com/company/my-executive-connect/
Watch the full episode (and more) on YouTube:
https://www.youtube.com/@ExecutiveConnect
Get The Full Executive Brief
Strategies and insights for leaders who refuse to settle – plus the Maverick Test to discover your archetype. https://executiveconnectexperience.com/get-the-full-brief
If you like the content, please do share, subscribe, and like the channel.
