Latest / The Resume Room with Fexingo: Resume Writing, Cover Letters, and Application Strategy / How to Explain a Failed Side Hustle on Your Resume
Transcript
- Lucas: So you spent 18 months building a side hustle — a boutique coffee subscription, let's say — and it folded. You lost twelve thousand dollars of your own money and a lot of weekends. Now you're applying for a marketing manager role and that eighteen-month block is staring back at you from your resume. Luna: And the instinct is to either hide it or apologize for it. Neither works. Lucas: Right. So today I want to walk through a specific framework for handling this. And I want to start with a data point. A 2025 survey from the career site Ladders found that 62 percent of hiring managers said they view a failed entrepreneurial venture more positively than a resume gap with no explanation at all. Luna: Sixty-two percent — that's not a small number. But it also means 38 percent see it as a red flag. Lucas: Exactly. And that's the tension. So the question is: how do you write this entry so it lands with the 62 percent and doesn't trigger the 38 percent? Let me start with a rule of thumb. Lead with the skill, not the story. Luna: Meaning don't lead with 'I started a coffee subscription that failed.' Lead with 'I built a customer acquisition channel from scratch.' Lucas: Yes. So in the resume, you list the venture under a section called maybe 'Projects' or 'Entrepreneurial Experience' — not 'Work History' if you're worried about scrutiny. And the first bullet point is something like: 'Launched a direct to consumer coffee subscription, acquiring 200 customers in six months with a customer acquisition cost of $35 per subscriber.' Luna: And you leave the part about it failing for the interview, if it comes up. Lucas: Right. The resume is not a confessional. It's a marketing document. So you show what you built and what you learned. The second bullet: 'Negotiated supplier agreements with three roasters, reducing cost of goods sold by 12 percent.' Third bullet: 'Managed end to end P&L for a $48,000 revenue run rate business.' Luna: And if the interviewer says, 'So why did it end?' — what's the script? Lucas: Short and skill-forward. You say something like: 'The unit economics didn't scale the way I projected. I learned a lot about margin structure and customer retention. Ultimately I decided to refocus on a role where I could apply those marketing skills in a more resourced environment.' Luna: That's good. It's honest but it frames the failure as a strategic decision and a learning moment. Lucas: Exactly. Now, there's a nuance I want to get into. Not every failed side hustle should go on the resume. If the venture was very short — say three months — and you didn't accomplish anything concrete, it might be better to just leave it off and treat the time as a gap. Luna: And if you do include it, where does it go on the page? Above your salaried job experience or below? Lucas: Below. Unless the skills you gained are directly more relevant to the job than your previous paid roles. For our marketing manager example, if the job requires experience with DTC marketing, then the side hustle might actually be the most relevant thing you've done. In that case, put it near the top under a 'Relevant Experience' header. Luna: But you're still not labeling it as a failure. You're labeling it by what you did, not by the outcome. Lucas: Exactly. The company name you put is your venture's name, not 'My Failed Startup.' I've seen people write 'Freelance Marketing Consultant' when they really mean 'I tried to start a business and it didn't work.' That's fine. You're framing the function, not the result. Luna: There's also the issue of dates. If the side hustle overlapped with a full-time job, some hiring managers might ask about time commitment. Lucas: Right. If you were working full-time at a marketing agency and also running the coffee subscription on nights and weekends, you don't want to suggest you were distracted. So you can note it as a 'concurrent project' in the description, or you can list it under 'Additional Experience' with a note like 'Evening and weekend venture.' Luna: Let me push back a little. There's a growing narrative on career TikTok and LinkedIn that failure is a badge of honor. 'Hire me because I failed and learned.' Does that actually work? Lucas: In my experience, it works in startups and tech companies where failure is culturally normalized. It works less in law firms, banks, traditional corporate environments. So you have to read the room. If you're applying to a company that talks about 'fail fast' in its values, you can lean into the learning story. If you're applying to a conservative firm, you might lead with the skills and let the failure come up organically. Luna: And then there's the question of the resume itself. Do you even have room for a side hustle that didn't succeed? If you have a solid five-year career with clear progression, the side hustle might just be noise. Lucas: I'd say if it's noise, cut it. But if it's the only place you demonstrated a skill the job requires — say, you managed a Facebook ad budget of $10,000 for the coffee subscription, and the job wants someone who can run paid social — then it's not noise. It's your best proof. Luna: So the framework really comes down to: does this entry make me a stronger candidate for this specific job? If yes, include it with skill-forward bullets. If no, leave it off. Lucas: That's the whole thing. And I'd add one more tactical piece: if you do include it, make sure the verbs are active and the metrics are specific. 'Launched,' 'negotiated,' 'managed,' 'reduced.' Don't say 'tried to start.' Say 'built and operated.' Luna: And if you're in an interview and they press on the failure, you stick to the script: what you learned, what you'd do differently, and how that makes you better at the job you're applying for. Lucas: Exactly. And honestly, if you handle it well, it can actually be a memorable point in your favor. Most candidates only talk about their successes. Someone who can talk about a failure with clarity and self-awareness — that stands out. Luna: Speaking of standing out — we've been doing this show for over a hundred episodes now, covering everything from explaining a termination to framing a career break. And we keep the show ad-free, no sponsors, no corporate voice. Lucas: Yeah, that's a deliberate choice. And it's possible because a small group of listeners chip in monthly through buy me a coffee dot com slash fexingo. It's not a big thing — just a way for people who find the show useful to help keep it going. Luna: And it genuinely makes a difference. So if you've gotten something out of an episode — maybe this one, maybe one of the earlier ones — that's the way to support it. Lucas: Right. So back to the resume. I want to leave you with one concrete exercise. Take the failed side hustle entry you're debating about. Write down three skills you actually used. Then write a bullet point for each one, with a number if you have it. Read it out loud. If it sounds like something you'd want to hire, keep it. If it sounds like an excuse, rewrite it. Luna: And if you can't get to three solid bullets, that's probably your sign to leave it off. Lucas: Exactly. The resume is not the place to process your feelings about the venture. It's the place to prove you can do the job.