@Override
protected void onMeasure(int widthMeasureSpec, int heightMeasureSpec) {
  int widthSize = MeasureSpec.getSize(widthMeasureSpec);
  int lineWidth = widthSize - getPaddingLeft() - getPaddingRight();

  // Change the text size until the largest line of text fits.
  while (lineWidth < calculateTextWidth()) {
    for (TextView textView : this.childViews) {
      float newSize = textView.getTextSize() - 1;
      textView.setTextSize(TypedValue.COMPLEX_UNIT_PX, newSize);
    }
  }

  super.onMeasure(widthMeasureSpec, heightMeasureSpec);
}

<com.my.widgets.ScalingTextViewGroup
  android:layout_width="0dp"
  android:layout_height="wrap_content"
  android:layout_weight="1"
  android:orientation="vertical"
  android:gravity="center_horizontal"
  >
    <TextView
        android:id="@+id/text_1"
        android:text="Text 1"
        android:textSize="20sp" />
    <TextView
        android:id="@+id/text_2"
        android:text="Text 2"
        android:textSize="18sp" />
    <TextView
        android:id="@+id/text_3"
        android:text="Text 3"
        android:textSize="18sp" />
    <TextView
        android:id="@+id/text_4"
        android:text="Text 4"
        android:textSize="18sp" />
</com.my.widgets.ScalingTextViewGroup>

@Override
protected void onMeasure(int widthMeasureSpec, int heightMeasureSpec) {
  int widthMode = MeasureSpec.getMode(widthMeasureSpec);
  if (widthMode != MeasureSpec.UNSPECIFIED) {
    int widthSize = MeasureSpec.getSize(widthMeasureSpec);
    int lineWidth = widthSize - getPaddingLeft() - getPaddingRight();

    // Change the text size until the largest line of text fits.
    while (lineWidth < calculateTextWidth()) {
      for (TextView textView : this.childViews) {
        float newSize = textView.getTextSize() - 1;
        textView.setTextSize(TypedValue.COMPLEX_UNIT_PX, newSize);
      }
    }
  }

  super.onMeasure(widthMeasureSpec, heightMeasureSpec);
}