The Heart & Hustle Podcast

Hosts: Evie McLeod & Lindsey Roman
Episode 460: We Wasted $300k+?!? 4 of The Biggest Mistakes We've Made in Business
Date: November 25, 2025

Overview

In this candid episode, Evie and Lindsey lay it all out—sharing four (plus a bonus) of the biggest financial and strategic mistakes they've made in their entrepreneurial journeys. Speaking directly to fellow creatives, dreamers, and doers, the hosts reflect on hard lessons, regrets, and what they would have done differently if they could go back and give advice to their younger selves. From burnout-inducing hustle to losing track of almost a year’s worth of paychecks, there’s no holding back as they detail the sometimes expensive schooling that comes with running a business.

Key Discussion Points & Insights

1. Hustling Without Strategy (03:06–10:27)

• Summary: Both hosts admit to working "sun up to sundown" in their early years, mistaking relentless hustle for productivity.
• Key Insight: Busyness does not always equate to moving the bottom line in your business; intention and strategic boundaries are crucial for sustainable growth and mental health.
• Notable Quotes:
  • “We operated out of the mindset that busy equals productive.” — Lindsey (04:43)
  • “Just because you can grind doesn’t mean you should always do it.” — Evie (09:14)
• Advice: Healthy hustle at the beginning can help with momentum, but it's vital to assess if the work is strategic and to establish boundaries before burnout hits.

2. Going Too Big, Too Fast (Evie Swim Case Study) (10:38–24:41)

• Summary: Evie opens up about the challenging experience with her swimsuit line, Evie Swim—overcommitting on inventory, SKUs, and ethical manufacturing in the U.S., which led to unanticipated costs and burnout.
• Key Insights:
  • Manufacturing in the U.S. limited options and drove up costs, while dealing with unethical manufacturers led to $50k+ lost in development alone.
  • Starting a product-based business with multiple styles and colors created complexity and financial strain.
  • Evie used all her own money (“I literally... just cringe a little bit looking back”) instead of spreading risk or starting with less.
• Notable Quotes:
  • “I wish that I had started with probably less designs... I went a bit too big right out the gate.” — Evie (16:10)
  • “Just because you can go big doesn’t mean you should start that way.” — Lindsey (23:24)
  • “I plan to... relaunch it... but this company requires a level of... energy and attention that I currently am not ready to give.” — Evie (20:11)
• Best Practices Learned:
  • Start smaller, validate demand, consider small-batch runs, seek external investors or partners, and don't risk personal savings beyond your risk tolerance.

3. Blind Outsourcing Without Clear Management (26:48–29:45)

• Summary: Both hosts reveal how they've wasted hundreds of thousands by hiring contractors and team members without clear performance metrics or regular evaluations.
• Key Insight: Trusting experts is good, but oversight, key performance indicators (KPIs), and regular accountability are essential.
• Notable Quotes:
  • “We were just throwing money at somebody...and never really checking up on them, never giving them a KPI.” — Lindsey (27:11)
  • “Sometimes the hard part is we were having regular meetings, so it felt like we were checking in…” — Evie (28:13)
• Actionable Advice: Every team member or contractor should have measurable goals and deliverables, and leaders must review, challenge, and, if necessary, change course or let people go.

4. Doing Too Much—Diversifying Before Building a Solid Foundation (29:48–37:20)

• Summary: The Heart team scaled rapidly—launching numerous products and services. While this brought initial financial success, it overwhelmed their systems and teams, stalling efforts to build evergreen revenue.
• Key Insight: Rapid expansion before perfecting backend systems for existing offerings leads to burnout, inefficiency, and financial strain.
• Notable Quotes:
  • “Just because you can do something or launch something else...does not necessarily mean that you should.” — Evie (29:58)
  • “I almost... hone in. Maybe don’t do the Instagram course, don’t do the reels course... just do the one thing.” — Lindsey (32:51)
  • “I think the thing that I regret is not that we offered more products, it’s that we didn’t get an evergreen system set up before offering a new product.” — Evie (33:22)
• Lessons Learned:
  • Build systems (especially for evergreen sales) before layering on more offers.
  • Avoid splitting focus and resources among too many simultaneous projects.

5. BONUS: Neglecting to Monitor Finances (38:33–43:55)

• Summary: In a surprise fifth mistake, they reveal a financial oversight: Evie stopped receiving her pay from the Heart company for over a year and didn’t notice.
• Key Insight: Even with bookkeepers and financial help, founders must regularly review accounts and distributions.
• Notable Quotes:
  • “Would recommend looking at your finances just every so often. Actually, more regularly.” — Lindsey (38:33)
  • “There could be also a life lesson... maybe you shouldn’t deserve to make a lot of money until you know how to steward it.” — Lindsey (40:22)
• Takeaway: Know your numbers, reconcile regularly, and take direct responsibility—even if you’ve hired professionals.

Notable Quotes & Memorable Moments with Timestamps

| Timestamp | Quote | Speaker | |-------------|-------------------------------------------------------------------------------|-----------| | 04:43 | “We operated out of the mindset that busy equals productive.” | Lindsey | | 09:14 | “Just because you can grind doesn’t mean you should always do it.” | Evie | | 16:10 | “I wish that I had started with probably less designs... I went a bit too big right out the gate.” | Evie | | 23:24 | “Just because you can go big doesn’t mean you should start that way.” | Lindsey | | 27:11 | “We were just throwing money at somebody...and never really checking up on them, never giving them a KPI.” | Lindsey | | 29:58 | “Just because you can do something or launch something else...does not necessarily mean that you should.” | Evie | | 32:51 | “I almost... hone in. Maybe don’t do the Instagram course, don’t do the reels course... just do the one thing.” | Lindsey | | 33:22 | “I think the thing that I regret is not that we offered more products, it’s that we didn’t get an evergreen system set up before offering a new product.” | Evie | | 38:33 | “Would recommend looking at your finances just every so often. Actually, more regularly.” | Lindsey |

Recap & Takeaways

• Hustle helped early on, but boundaries and strategy are essential—avoid mistaking busyness for effectiveness.
• Go big only after careful validation—start small, reduce inventory and risk, and don’t overextend your resources.
• Clear metrics, communication, and oversight are vital when outsourcing.
• Build strong systems before diversifying; focus beats doing everything.
• Regularly review your financials—never assume someone else is catching errors for you.

Listener Invitation

The hosts close by emphasizing their willingness to be vulnerable and honest, hoping these costly (sometimes embarrassing) lessons save listeners their own money and stress. They invite feedback on this level of transparency and ideas for future topics, highlighting their group DM as a community resource.

Evie: “Please don’t make our mistakes.” (43:22)
Lindsey: “This was frankly a coaching call for you because you just learned so much from our mistakes.” (43:16)

To connect or offer feedback:

• DM the hosts or join the Heart & Hustle group chat community.
• “If you like super vulnerable, we made mistakes, Lindsay and I. Heavy.” – Lindsey (44:12)

End of Summary