Startups struggle, AI to avoid, and job search in 2025 | Intent, 020

Intent is all about helping talent in tech become more intentional with their career by becoming more informed and more fluent about the goings-on within + around the industry. We welcome your feedback!

Today's agenda:

• What the Bench shutdown ACTUALLY means for startups

• What NOT to do with AI in 2025

• Ways you’re sabotaging your 2025 job search

The Bench Bombshell

Recap, ICYMI: Bench, the VC-backed accounting startup serving 35,000+ small businesses, just showed us how quickly things can unravel in tech. On December 27th, they abruptly announced their platform would shut down, leaving customers scrambling for their financial data just before tax season.

The plot thickened quickly:

• Former CEO Ian Crosby blamed the board's decision to replace him

• Customers were given until March 2025 to download their data

• Then, Employer dot com swooped in with an acquisition (price undisclosed)

But here's what's interesting: Bench's "$60M Series C" wasn't what it seemed. It was actually $37M equity + $23M venture debt, highlighting a broader industry issue.

Venture debt can be deadly when things go south. These are special loans for VC-backed startups. They let the company get equity-free capital, they are easier to qualify for thanks to tech-friendly banks that evaluate the deal based on the VCs involved rather than the fundamentals, and they can be used flexibly (unlike traditional loans, which may be particular to a specific business purpose).

BUT — they come with strict covenants requiring companies to:

• Maintain minimum cash balances

• Hit revenue/growth targets

• Stay under maximum burn rates

• Keep specific board compositions

Break these covenants? Lenders can demand immediate repayment and freeze accounts - exactly the kind of sudden death we just witnessed.

Watch this space: According to Carta data, companies that raised $50M+ in 2021-2022 are hitting their make-or-break moments. Bench won't be the last surprise shutdown we see in 2025.

Three Things NOT to Do With AI in 2025

Yes, AI is going to keep getting better. But don’t expect 2025 to be the year you can outsource all of your mental heavy-lifting to a large language model. Here are three “don’ts”:

1. Deep or Comparative Research
Tools like Perplexity, Exa, and ChatGPT plugins claim to do complex research and web- or Reddit-based product comparisons for you. But if you’re trying to find that obscure bit of feedback (like that random post from user dogs_r_kewl_1991) describing an exception to a credit card’s 3% cashback rule), you might be better off scanning yourself.

AI’s retrieval is still limited when it searches the web. It’s pulling the same results any human can access, but then is deciding what seems “worthy” and fits within its token limitations (size of request + response), meaning you lose the potential for the manual “serendipity” moment. Let AI serve as an augment, but keep a human eye on the details.

2. Intense Emotional or Psychological Reliance
We’ll keep hearing about AI therapy and increasingly-awesome voice-based “companions” for deeper conversations. However, most LLMs remain highly sanitized, or “neutered.” That’s for good reason: they don’t yet have the nuance for these companies to let them loose in vulnerable situations. So, the system instructions and tuning will always drive these models to the “average” response to avoid chaos. We’ve already seen AI chatbots cause emotional crises in 2023 and 2024.

While they can spit out basic mental-health tips, your mileage may vary if you need real human-level wisdom or if you’re looking for advice that departs from the safe, consensus boilerplate. Use it as a sanity check rather than as your primary BFF.

3. Unsupervised Long-Chain Tasks
We’ve seen an explosion in use of automation tools (Zapier, Make) and “AI agents” that promise to handle scheduling, outreach, or multi-step tasks. They can be impressive. But the biggest risk is all the “near-miss” moments.

Each call to an AI in a multi-step chain is siloed and has a particular task. An email might get sent to the wrong person because an AI call didn’t expect the primary contact to be CC’d instead. A personalized sales email might say “saw that you have a LinkedIn account - cool!” because it didn’t have anything else to say, but it had to spit out an answer.

Until these chain-of-thought agents get 5–10x better at context (some companies are working on orchestration, aka “manager agents”) keep a human in the loop for quality control.

Become the AI Whisperer: When to Bully, Flirt, Teach, etc. — free, live workshop on Monday, Jan. 6 — recording will be sent to anyone who RSVPs. RSVP!

Three Things Not to Do in Your 2025 Job Search

If you’re kicking off a job hunt in this super-competitive market, here are three faux pas to avoid:

1. Let AI Do All the Talking
Don't over-rely on AI tools. Skip the AI resume makers, cover letter generators, and application automation. They produce generic, obvious results that scream "AI-generated" to recruiters. Instead, use ChatGPT strategically - for document critique, research, and interview practice.

Remember: your application material will exist permanently in the applicant tracking systems (ATS) that you submit to — do you really trust an AI wrapper to apply to the right jobs and answer questions in a way that doesn’t seem off?

2. Wing It on “Why You?”
From the first recruiter screen onward, show that you’ve genuinely thought about why you’re a fit for this company. Show them how your war stories could solve their immediate or near-term challenges — it’s analogies all the way down.

If you’re a product manager who has worked on payments at Shopify, and you’re interviewing at Uber for the driver experience team, stretch to showcase that relevance: tell stories anchored around how your prior experience with streamlined checkout features boosted your customer satisfaction, and that could be applied to the rider app > make riders happier > lead to better UX for drivers.

3. Ask “Any Hesitations About My Candidacy?”
This question has become a cliche, and rarely does it bring about a magically honest conversation that helps you fix negative perceptions on the spot. Most interviewers won’t reveal what they’re really thinking, and you could inadvertently end the interview on a sour note. Instead, ask forward-looking or strategic questions that showcase your intelligence and enthusiasm.

3 Steps to a Stellar 2025 Job Search — free, live workshop on Thursday, Jan. 9 — recording will be sent to anyone who RSVPs. RSVP!

That’s all for now – may your 2025 be filled with fewer unexpected shutdowns and more strategic AI adoption.

Sent with Intent,
By Free Agency