Why $1M ARR Doesn't Guarantee Success

\"You gotta always be looking at like two steps ahead, three steps ahead and being really thoughtful about how you create option value... As soon as you think it's set or it's easy or the next step is guaranteed, that's when you trip up.\"

• Never assume success is guaranteed at any stage.
• Continuously plan and prepare for future challenges.
• Maintain a proactive mindset to navigate obstacles.

\"By the end, we had one path and if that path got closed off, it was game over... I so wish that we'd been more thoughtful about creating additional pathways.\"

• Develop multiple strategies to achieve your goals.
• Be prepared for unexpected obstacles by having alternative plans.
• Diversification can safeguard against failures in any single approach.

\"Do you regret starting it? Hell no, absolutely not. If you had told me three years ago that this would be the outcome, I think I still would have left my cushy corporate job to do this... I learned so much the last three years that I just wouldn't have got, I wouldn't have gotten those experiences any other way.\"

• The startup journey offers valuable learning experiences.
• Entrepreneurial pursuits can be rewarding beyond financial success.
• Embracing risks can lead to personal and professional growth.

\"We got all the way through confirmatory due diligence... Funding Docs went out, I signed the Funding Docs. And I think they got cold feet... I wish they had taken a different approach and told us earlier because, you know, time is the greatest resource you have as a founder.\"

• Fundraising deals are not secured until funds are received.
• Always prepare alternative plans in case deals fall through.
• Communicate openly with investors to minimize surprises.

\"You can't support that cost basis on a subscale business... our model was really predicated on getting to meaningful scale quickly... It was just taking a really long time to get that flywheel going.\"

• Fixed costs require sufficient revenue to offset.
• Delays in scaling can strain finances and threaten viability.
• Plan for realistic timelines to reach necessary scale.

\"I think a lot of times founders of startups that don't make it... they really manage the narrative around it. I respect people who want to do that, but I also think it's valuable for founders to have these types of conversations about why didn't it work.\"

• Sharing failures helps others learn and avoid similar mistakes.
• Open discussions can foster a supportive startup community.
• Honesty builds credibility and personal growth.

\"Oftentimes what we hear from a brand is this is really cool. I love it, but not right now... We struggled to create urgency and... it's a very tough hill to climb with those SMBs.\"

• Lack of urgency leads to prolonged sales cycles and delayed revenue.
• Identify and address the immediate pain points of customers.
• Develop compelling value propositions that encourage prompt action.

\"Our monthly burn was around half a million... we had some fairly big fixed costs. Our monthly fee to our sponsor bank was six figures... you can't support that cost basis on a subscale business.\"

• Lending businesses have high fixed costs that require scale to offset.
• Regulatory compliance adds complexity and expenses.
• Ensure you can achieve sufficient scale quickly to cover fixed costs.

\"I would start with the most capital light version of the thing that you're trying to build to really, really confirm you have product market fit. And I think we told ourselves a few times, oh, we've got it, we've got product market fit. And I, if I'm being really honest with myself, I don't know that we ever fully had that then.\"

• Test your core assumptions with minimal investment.
• Avoid large fixed costs before validating your market.
• Iterate quickly based on early feedback.

\"I think we, we kept telling ourselves, let's give it one more month, let's give it one more month. Let's get some more data. And I think, uh, keep in mind too, the signals we're getting from prospects are generally positive, right?\"

• Underestimating sales cycles can delay revenue and traction.
• Pivot quickly if your initial customer segment isn't responding.
• Create urgency in your sales process for faster adoption.