Sometimes the hard way is the only way to learn. But when you’re building a business, those hard-earned lessons can be major time sinks that may end up costing you your savings — or worse yet, your reputation.
To help early-stage startups avoid costly mistakes, we asked leaders in the Chicago tech community what advice they have for newcomers. The insights they offered this year covered every aspect of growing companies and gaining traction in the marketplace, from recruiting to customer service, insurance, and search engine optimization.
Here’s what they had to say.
Help your customers help themselves
Customer service can take a major toll on your resources, so before launching a new product you need to ensure you have everything in place to mitigate the inevitable flood of questions. One way to do that, according to Nicole McCloud of
“When you’re a new company, you need to help your clients find the answers they need quickly or they could leave and go to someone else,” said McCloud. “Take the time to build out a robust knowledge base to empower your customers to help themselves and get immediate answers to their questions.”
For more customer service tips, check out “5 need-to-know customer service tips before you launch your product”
How to compete with larger companies for interns
“Really let candidates know they're going to make a difference in the company,” said
If you’re looking to attract candidates who are also considering enterprise opportunities, Weingarten said to emphasize how the hands-on aspect of working for a startup can foster a more immersive learning experience than an internship with a large company. All of his interns have worked on features that ended up in the finished product — an achievement that’s harder to list on a resume if you’re one of 500 interns during a single summer.
For more recruiting advice from Weingarten, check out "4 tips to help startups land top candidates at a career fair"
Laser-focus on the problem you’re solving
Although originally offered by
“We knew it could be confusing to explain every idea we’d ever had, so by keeping conversations on our one focus, it allowed us to demonstrate our mission better,” said Vargas Wrigley.
For more advice from Vargas Wrigley and other Techstars insiders, check out “7 insider tips on how to get in and thrive with Techstars”
Don’t make hires you’ll come to regret later
When your company is rapidly growing, you may find yourself tempted to take a chance on an applicant you wouldn’t otherwise have hired.
“Finding the right person is always more important than finding a person,” said Cutler.
Having been involved in organizations that have grown faster than they were prepared for in the past, he speaks from experience. Besides productivity losses, Cutler points out that bad hires can have a negative impact on culture, and ultimately future growth.
For more advice on growing responsibly, check out “4 Chicago tech companies weigh in on how to grow your startup responsibly”
Realistically speaking, many early-stage startups are at risk of going under if a major unforeseen circumstance arises. From data breaches to problems with your code, insurance can provide you with peace of mind and a ready-made legal defense team.
“When tech companies start out, it’s typically one person with an idea,” said Kirsten Charlton, AVP of
For more on insurance for startups, check out “5 things tech startups need to know after they’ve landed their first round of funding”
Make sure potential customers find you
Colin Guidi, Director of Search Engine Optimization (SEO) at
Instead, SEO is most beneficial when it’s used as an ongoing engagement. That means developing fresh and frequent content updates that work for today and predict the needs of tomorrow.
“Your site content will change,” Guidi said. “You might acquire an offering and need help promoting it. An algorithm update will come along and knock you ship/website off course. SEO should not be reactive but rather proactive.”
For more on SEO, check out “Debunked: The truth behind the top 5 SEO myths”
Bonus: The worst advice Punchkick Interactive's CEO ever heard
This year, we also published a list of the worst pieces of advice Chicago startup leaders ever received. Here’s
"I received some awful advice from someone close to me a few years ago. This person told me that it would be a big mistake to let my employees see me as a peer, as it would 'erode my leadership ability' with them. He also advised me to keep a certain amount of distance between myself and our staff, so that they wouldn't take advantage of our friendship and cut corners. I now realize that he was completely projecting his issues onto me. Many of the folks I work with at Punchkick are my closest friends in the world, and I thrive on our working together as peers, friends, and in many cases, like family. I've found that by opening up about both the good and bad issues facing the company, I'm able to rally excitement and a team dynamic I've never seen in a company before. I can bring my whole self to work, flaws and all, and find support and strength in the team around me. Nearly every step I've taken to be transparent and vulnerable with those I work with has rewarded me in ways that I can't describe. The camaraderie and sense of family at Punchkick is worth more than any other professional accomplishment I've experienced."
For more bad advice, check out “4 Chicago startup leaders share the worst business advice they've ever heard”
Photos via Shutterstock, mLevel and Techstars.
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