08/18/15 | Founders, OOO

Pregnant? Tips for Bootstrapping, Fundraising and Running Your Business

As a team of three women founders of Plango, a travel tech startup, we have received heaps of encouragement and support from family, friends, mentors and advisors.
It’s awesome seeing the upward trend of fellow women entrepreneurs and investors like Jonathan Sposato advocating for equality. Being located in Silicon Valley, I honestly didn’t feel like there was any more pressure on me than my male counterparts… until I found out I was pregnant.

Like many women, I want it all! And starting a family isn’t going to change my dreams of turning my idea into a business.
Once I started researching for advice, it dawned on me that pregnancy is not something that is openly discussed in the entrepreneur world. I want to change that. Now that I’ve been through nine months of battling nausea, fatigue and swelling while bootstrapping our product, I want to share the details of how to persevere and start the conversation.
It was tough, but rewarding!

My support crew

When I found out I was pregnant, my husband and I were ecstatic. Naturally as all soon-to-be parents do, we started talking about how everything would change and how we would juggle it all.
What really helped was recognizing that I wasn’t in this alone.

  • My husband who has a stable income and is supportive of my ambition
  • An extra helping hand, in my case my mother-in-law who is excited to be a grandma
  • Two co-founders who are happy for me and ready for the challenge


When you’re in the very early stages like us, the best way to operate is bootstrapping. But when you’re starting a family and a company, this brings up the age old issue of “show me the money.”
I’m extremely lucky to have an awesome husband with a stable full-time job and benefits I can piggy-back on. Without this, it would have been too risky to venture forth.
But don’t forget that there are other sources of income that include contracting on the side a few days of the week, investment income, or even living off savings for a predefined timeframe.

Flexible schedule

Pregnancy comes with a multitude of doctor’s appointments and birthing classes that will throw any kind of attempt at a 9-to-5 out the door.
I often found myself syncing up with my co-founders through Google Hangout screenshare and having impromptu brainstorming sessions at 1 a.m. Being a pregnant entrepreneur means working when you can — but taking frequent bathroom breaks while looking out for yourself and your baby’s health.

Tenacious planning

Get right on making a rough adaptable plan for the remainder of the pregnancy and months after that. There is no such thing in the pregnancy/mom-world that is set in stone. Planning ahead allows you to delegate tasks and prepare for your well-deserved maternity leave.
For a tech product like Plango, sprints and release dates planned out way ahead of time is crucial. Targetprocess and Trello are great free tools to help you with this.

Talking to investors

Once you have the day-to-day operations in order, you’ll need to obtain funding. The main decisions to be made here is whether to pitch during or after the pregnancy and how to bring up the elephant in the room.
To test the waters, I set up meetings with a few investors. As I gave them the pitch on Plango, I was amused to see that I was right and everyone ignored my obviously large belly. I decided to point out that I was pregnant after the pitch to see what response I would get.
Luckily, one investor gave me some solid advice and told me to own it by working my pregnancy into my pitch. By doing so, I would have the chance to answer any concerns investors have for the future of Plango.

How to work your pregnancy into your pitch

  • Integrate your pregnancy into your pitch story
  • Use your pregnancy as an example, eg. Plango’s ability to share plans for my babymoon or traveling with kids
  • Address maternity leave in the roadmap

You’re going to be a mom! Although it will be challenging, it can totally be done with patience and the help of caffeine (under 200mg). Let your confidence shine through and take it one step at a time.
Lead by example and show your child that women can be both a loving mother and successful entrepreneur. Enjoy the journey!

About the guest blogger: Jessi Chow is the CEO and Cofounder of Plango, a startup that makes it easy to find and use itineraries from other travelers, saving you months of research time. Her expertise in UX design and gamification gives her a fresh, fun perspective into the travel industry. Follow Plango on Twitter at @plango_us.

Maci Peterson Philitas

Maci Peterson Philitas

Maci is passionate about building businesses that help people be the best version of themselves. Her goal is to make an impact and lead change through every opportunity that comes her way. Maci is the CEO and co-founder of On Second Thought (OST), the definitive delay-recall mechanism for mobile communications platforms. As an entrepreneur and respected thought leader, She's a frequent lecturer, subject-matter expert, and advisor on entrepreneurship, innovation, and diversity initiatives. Under her leadership, OST has expanded to 190 countries; secured multiple patents; and now licenses its highly scalable software system across several industries. She's been named to several notable lists, including SF Business Times 40 Under 40 list; BBC 100 Women; Inc. Magazine’s 30 Under 30; and Washington Business Journal’s 40 Under 40.

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