Episode 90: Lessons Learned Going From Solo Freelancing → Scaling an Agency → Selling It → Founding a SaaS Startup, with Jesse Hanley

By Zach Swinehart

In this episode, Zach talks to Jesse Hanley from Bento – the email marketing tool.

In today’s episode, you’ll find out how Jesse went from solo freelancer to scaling a 25-person agency, then selling it all and starting a SaaS email marketing product.

Jesse talks about the challenges of scaling an agency including client lead flow, having a lean team, and the benefits of a simple business model.

We dive deep into how being genuinely helpful online can lead to big customers, and whether you should chase scaling your business or focus on doing your best work every day.

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AI-Generated Summary:

  • 0:00 – 2:00 — Zach introduces Jesse, who founded Bento, an email marketing software they use. Zach praises Bento and mentions switching from Convert Kit.
  • 2:00 – 4:00 — Zach asks Jesse about his early freelancing days. Jesse shares his experience working in a supplement company in Australia before transitioning to consulting.
  • 4:00 – 6:00 — Jesse talks about how he moved from retail to tech within the same company. He shares how he was proactive in suggesting and implementing tech solutions.
  • 6:00 – 8:00 — Zach and Jesse discuss the pros and cons of working in a small, fast-moving company versus a larger, more bureaucratic one. Jesse mentions the company made millions in revenue.
  • 8:00 – 10:00 — Jesse explains his transition to remote work. He shares tips on how to negotiate remote work and how he started picking up other clients.
  • 10:20 – 12:00 — Zach talks about how he got into niche communities that interest him, like Nomad List, and how that led to great clients.
  • 12:00 – 14:00 — Zach discusses his early career goals, focusing on survival and fulfilling his dream of working remotely.
  • 14:00 – 16:00 — Zach shares the importance of being active in online communities and building relationships to get clients.
  • 16:00 – 18:00 — Zach talks about being a “helpful neighbor” online and how it led to business opportunities over time.
  • 18:00 – 20:00 — Zach advises on the balance between being helpful and self-promotion in online communities.
  • 20:18 – 22:18 — Zach talks about the importance of genuine engagement in online forums for SEO and how it brings in leads.
  • 22:18 – 24:18 — Zach discusses the growth of his team and how he started to bring on more people as the workload increased.
  • 24:18 – 26:18 — Zach shares the challenges of managing a growing team and how it led to stress and mistakes.
  • 26:18 – 28:18 — Zach talks about pivoting his business model to focus on what he enjoys, which is hiring writers for clients.
  • 28:18 – 30:18 — Zach explains how the new business model was easier to sell and manage, and also touches on the topic of value-based pricing.
  • 31:00 – 33:00 — Zach talks about the value of his productized service and how it reduces risk for clients.
  • 33:00 – 35:00 — Zach explains the benefits of his service, like quick results and easy feedback.
  • 35:00 – 37:00 — Zach discusses how his service is low-risk and cost-effective compared to traditional SEO agencies.
  • 37:00 – 39:00 — Zach shares the structure of his team and how they handle content creation and editing.
  • 39:00 – 41:00 — Zach talks about his sales strategy, emphasizing the importance of being easily reachable for calls.
  • 41:00 – 43:00 — Zach discusses his client qualification process and the importance of not hard-selling.
  • 43:00 – 45:00 — Zach talks about the challenges of scaling an agency and the need for a consistent lead flow.
  • 45:00 – 47:00 — Zach shares how his new business model reduced stress and increased predictability.
  • 47:00 – 49:00 — Zach explains the benefits of having a lean team and a simplified service offering.
  • 49:00 – 51:00 — Jesse describes the structure of his team, highlighting the minimal management needed.
  • 51:00 – 53:00 — Jesse talks about the flexibility and understanding between clients and contractors, even during personal issues like breakups.
  • 53:00 – 55:00 — Jesse and Zach discuss the use of Basecamp for project management and how it streamlines communication.
  • 55:00 – 57:00 — Zach explores the idea of productized services and Jesse shares how his business model focuses on what he enjoys.
  • 57:00 – 59:00 — Zach and Jesse delve into the challenges of scaling and the importance of markup in pricing.
  • 59:00 – 01:01:00 — Jesse advises on the need for a competitive edge and how to make everyone in the business model happy.
  • 1:00:58 – 1:02:58 — Jesse talks about the importance of having good margins in business and making the price a “no-brainer” for clients.
  • 1:02:58 – 1:04:58 — Zach agrees and adds that writing is integral to business, making it a no-brainer to keep the service.
  • 1:04:58 – 1:06:58 — Jesse discusses why his business model works, focusing on value and low churn rates.
  • 1:06:58 – 1:08:58 — Zach and Jesse talk about the benefits of a simple business model and how it helped Jesse.
  • 1:08:58 – 1:10:58 — Jesse shares his experience with his team and how he should have listened to his gut about working with a specific group.
  • 1:11:00 – 1:13:00 — Jesse talks about the importance of filtering clients and team members for better mental health.
  • 1:13:00 – 1:15:00 — Jesse shares stories of good and bad client interactions, emphasizing the value of kindness.
  • 1:15:00 – 1:17:00 — Jesse discusses how giving team members permission to communicate boosts their confidence.
  • 1:17:00 – 1:19:00 — Zach and Jesse explore effective communication structures for freelancers, focusing on automated check-ins.
  • 1:19:00 – 1:21:00 — Jesse advises integrating into the client’s existing communication tools and keeping updates short and frequent.
  • 1:21:00 – 1:23:00 — Jesse and Zach discuss the importance of clear communication in freelancing and how it led Jesse to hire Anya.
  • 1:23:00 – 1:25:00 — Zach talks about automating tasks in Zapier and emphasizes that consistent communication has been key to Jesse’s success.
  • 1:25:00 – 1:27:00 — Jesse shares the journey of Bento, from its experimental phase to becoming a competitive email marketing tool.
  • 1:27:00 – 1:29:00 — Jesse talks about selling his agency and how it allowed him to focus on Bento, eventually surpassing the agency’s revenue.
  • 1:29:00 – 1:31:00 — Zach asks what made Jesse confident enough to double down on Bento, and Jesse explains it was a mix of timing and market need.
  • 1:31:00 – 1:33:00 — Zach questions Jesse on validating a product before investing time and resources. Jesse discusses the importance of “taste” in product development.
  • 1:33:00 – 1:35:00 — Jesse talks about how personality influences the type of products you can develop. Zach outlines a potential roadmap for growing an agency into a SaaS business.
  • 1:35:00 – 1:37:00 — Jesse shares insights on the value of specialized hosting services. He mentions a friend who found success by offering an “incident team” for website issues.
  • 1:37:00 – 1:39:00 — Zach and Jesse discuss the benefits of a hybrid SaaS and service model. Jesse talks about how managed accounts helped him improve his product.
  • 1:39:00 – 1:41:00 — Zach praises the hybrid model for its financial viability and customer feedback. Jesse emphasizes that close customer interaction helps improve the product.
  • 1:42:00 – 1:44:00 — Jesse talks about the power of being helpful online and how it led to a $2K/month customer.
  • 1:44:00 – 1:46:00 — Zach and Jesse discuss the importance of targeting clients you care about for long-term success.
  • 1:46:00 – 1:48:42 — Jesse advises focusing on doing your best work each day instead of getting lost in scaling goals.